洪伯誠 教授 Hong, Bor-Cherng                           Professor

Date of employment: Aug. 1, 1994

Specialty: Synthetic Organic Chemistry, Medicinal Chemistry

TEL (O): (886-5) 272-0411
ext. 66404

Email: chebch@ccu.edu.tw

Lab Webpage

 

 

到校日期:8381

專長領域:有機合成化學、藥物合成

 

聯絡電話:(05) 272-0411 ext. 66404

電子信箱:chebch@ccu.edu.tw

研究室:Rm 514

實驗室網頁

 

 

B.S. in Chemistry, Tunghai University, 1984

M.S. in Chemistry, National Taiwan University, 1986

(Member of Phi Tau Phi Scholastic Honor Society)

Ph. D. in Chemistry, University of Chicago, 1993

Research Assistant, Univ. Pennsylvania, 1990-1992

Postdoc Research Associate, Harvard Univ., 1993-1994

Assoc. Professor, National Chung Cheng Univ. , 1994-1999

Professor, National Chung Cheng University, 1999-2002

Chairperson of Department of Chemistry and Biochemistry, 2012-2015

 

 

學士 東海大學化學系理學士 (1984)

碩士 國立台灣大學化學系碩士 (1986)

(斐陶斐榮譽學會會員)

博士 美國芝加哥大學化學系博士 (1993)

美國賓州大學化學系論文研究 (1990-1992)

美國哈佛大學化學系博士後研究 (1993-1994)

國立中正大學化學系副教授 (1994-1999)

國立中正大學化學系教授 (1999-2002)

國立中正大學化生系教授 (2002-)

中正大學化學暨生物化學系主任 (2012-2015)

Research Interests

Organic Photochemistry

Total Synthesis of Natural Products

New Synthetic Methodologies

Asymmetric Reactions

Medicinal Chemistry

 

 

研究重點

有機光化學

有機天然物合成

創新有機反應的開發

不對稱有機反應的開發及應用

藥物化學

Selected Publications 代表著作

  • Wei-Lun Huang, Arun Raja, Bor-Cherng Hong,* and Gene-Hsiang Lee, “Organocatalytic Enantioselective Michael−Acetalization−Reduction−Nef Reaction for a One-Pot Entry to the Functionalized Aflatoxin System. Total Synthesis of (−)- Dihydroaflatoxin D2 and (−)- and (+)-Microminutinin” Organic Letters, 2017, 19, 3494−3497

  • Vishal M. Sheth, Bor-Cherng Hong,* Gene-Hsiang Lee, “Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis” Org. Biomol. Chem. 2017, 15, 3408 – 3412.

  • Chia-Chueng Chen, Bor-Cherng Hong,* Wen-Shan Li,* Tzu-Ting Chang, and Gene-Hsiang Lee, “Synthesis Of Biologically Active Bis(Indolyl)Methane Derivatives by BisindoleAlkylation of Tetrahydroisoquinolines with Visible-Light Induced Ring-Opening Fragmentation” Asian J. Org. Chem. 2017, 6, 426–431.

  • Bor-Cherng Hong,* “Small Organic Moleculecatalyzed Reactions” in Encyclopedia of Physical Organic Chemistry, Zerong Wang Ed.; Chapter 24, p 1223–1298, John Wiley & Sons, Inc. 2017 April. ISBN 978-1-118-46858-6 DOI: 10.1002/9781118468586.epoc2024

  • Chieh-Hung Peng, Bor-Cherng Hong,* Arun Raja, Chun-Wei Chang and Gene-Hsiang Lee, “Constructing Densely Functionalized Hajos–Parrish-type Ketones with Six Contiguous Stereogenic Centers and Two Quaternary Carbons in a Formal [2+2+2] Cycloaddition Cascade” RSC Advances, 2016, 6, 95314–95319.

  • Arun Raja, Bor-Cherng Hong,* Ju-Hsiou Liao, and Gene-Hsiang Lee “Organocatalytic Enantioselective Michael−Michael−Henry Reaction Cascade. An Entry to Highly Functionalized Hajos−Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons” Organic Letters, 2016, 18, 1760−1763.

  • B.-C. Hong* in, “Constructing Molecular Complexity and Diversity by Cycloaddition Reactions of Fulvenes” in Cross Conjugation: Modern Dendralene, Radialene and Fulvene Chemistry, Henning Hopf, H. and Sherburn, N. S., Ed.; Chapter 7, p 249–300, Wiley, 2016 April. ISBN 978-3-527-33437-7

  • Chia-Hsin Lin, Bor-Cherng Hong,* and Gene-Hsiang Lee “Asymmetric Synthesis of Functionalized Pyrrolizidines by an Organocatalytic and Pot-economy Strategy” RSC Advances, 2016, 6, 8243–8247. 

  • Van-Wei Yang, Bor-Cherng Hong,* Hsin-Kai Kao, Ting-Hsun Tu, Jiun-Yi Shen, Chi-Lin Chen, Gene-Hsiang Lee, Pi-Tai Chou*, "One-Pot Dichotomous Construction of Inside-Azayohimban and Pro-Azayohimban Systems via an Enantioselective Organocatalytic Cascade; Their Use as a Model to Probe the (Aza-)Indole Local Solvent Environment." Organic Letters, 2015, 17, 5816–5819.

  • Bor-Cherng Hong*, Arun Raja, Vishal M. Sheth ”Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies” Synthesis, 2015, 47, 3257–3285.

  • Cheng-Wei Lin, Bor-Cherng Hong,* Wan-Chen Chang, Gene-Hsiang Lee, "One-pot A New Approach to Nitrones through Cascade Reaction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis." Organic Letters, 2015, 17, 2314–2317

  • Nitin S. Dange, Bor-Cherng Hong,* and Gene-Hsiang Lee, “One-pot Biomimetic Total Synthesis of Yuehchukene via the Organocatalytic Alkylation-cyclization Process of a Sterically Encumbered α-Alkyl Enal” RSC Advances, 2014, 4, 59706–59715.

  • Arun Raja, Bor-Cherng Hong,* and Gene-Hsiang Lee, “Organocatalytic Enantioselective Michael–Michael–Michael–Aldol Condensation Reactions: Control of Five Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Highly Functionalized Hexahydrophenanthrenes” Organic Letters, 2014, 16, 5756−5759.

  • Teh-Chang Chou and Bor-Cherng Hong, “Octacarbonyldicobalt (Second Update, pp 12–26)” Encyclopedia of Reagents for Organic Synthesis [Online], John Wiley & Sons Ltd. DOI: 10.1002/047084289X.ro001.pub3
    http://onlinelibrary.wiley.com/book/10.1002/047084289X [2014/5/28].

  • Dai-Huei Jhuo, Bor-Cherng Hong,* Chun-Wei Chang, and Gene-Hsiang Lee, “One-Pot Organocatalytic Enantioselective Michael–Michael–Aldol–Henry Reaction Cascade. A Facile Entry to the Steroid System with Six Contiguous Stereogenic Centers” Organic Letters, 2014, 16, 2724–2727

  • B.-C. Hong,* N. S. Dange, “Cascade Reactions in Stereoselective Synthesis” in Stereoselective Synthesis of Drugs and Natural Products, Vasyl Andrushko and Natalia Andrushko, Ed.; Chapter 21, p 581-621, Wiley, 2013 October. ISBN 978-1-118-03217-6.

  • Bor-Cherng Hong, “Organocatalyzed Cycloadditions” in Enantioselective Organocatalyzed Reactions II, Rainer Mahrwald, Ed.; Chapter 3, p 187-244, Springer, 2011. ISBN 978-90-481-3866-1.

  • Bor-Cherng Hong,* Wei-Kai Liao, Nitin S. Dange, and Ju-Hsiou Liao, “Sequential Asymmetric Catalysis in Michael–Michael–Michael–Aldol Reactions: Merging Organocatalysis with Photoredox Catalysis in a One-Pot Enantioselective Synthesis of Highly Functionalized Decalines Bearing a Quaternary Carbon Stereocenter" Organic Letters, 2013, 15, 6258-6261.

  • Nitin S. Dange, Bor-Cherng Hong,* Chih-Ching Lee, and Gene-Hsiang Lee, “One-Pot Asymmetric Synthesis of Seven-Membered Carbocycles Cyclohepta[b]indoles via a Sequential Organocatalytic Michael/Double Friedel–Crafts Alkylation Reaction " Organic Letters, 2013, 15, 3914-3917.

  • Bor-Cherng Hong,* Wei-Kai Liao, Nitin S. Dange, and Ju-Hsiou Liao, “One-Pot Organocatalytic Enantioselective Domino Double-Michael Reaction and Pictet-Spengler–Lactamization Reaction. A Facile Entry to the “Inside Yohimbane” System with Five Contiguous Stereogenic Centers" Organic Letters, 2013, 15, 468-471.

  • Bor-Cherng Hong,* Ding-Jyun Lan, Nitin S. Dange, Gene-Hsiang Lee, and Ju-Hsiou Liao, “Organocatalytic Enantioselective Michael-Henry acetalization of Glutaraldehyde and 2-Nitro-3-arylprop-2-enol. A Facile Entry to the 3-Oxa-bicyclo[3.3.1]nonan-2-ones with Four Consecutive Stereogenic Centers " Eur. J. Org. Chem. 2013, 2472-2478.

  • Bor-Cherng Hong,* Nitin Dange, Po-Jen Yen, Gene-Hsiang Lee, and Ju-Hsiou Liao, “Organocatalytic Asymmetric Anti-Selective Michael Reactions of Aldehydes and the Sequential Reduction/Lactonization/Pauson–Khand Reaction for the Enantioselective Synthesis of Highly Functionalized Hydropentalenes" Organic Letters, 2012, 14, 5346-5349.

  • Bor-Cherng Hong,* Po-Yuan Chen, Prakash Kotame, Pei-Ying Lu, Gene-Hsiang Lee and Ju-Hsiou Liao, “Organocatalyzed Michael–Henry reactions: Enantioselective synthesis of cyclopentanecarbaldehydes via the dienamine organocatalysis of a succinaldehyde surrogate " Chemical communications, 2012, 48, 7790-7792. (封面故事 Front Cover Picture).

  • Bor-Cherng Hong,* Che-Sheng Hsu and Gene-Hsiang Lee, “Total synthesis of (+)-galbulin via organocatalytic domino Michael–Michael–aldol condensation" Chemical communications, 2012, 48, 2385-2387. (封面故事 Front Cover Picture)

  • Bor-Cherng Hong,* Nitin Dange, Chun-Feng Ding, Ju-Hsiou Liao, “Organocatalytic Michael–Knoevenagel–Hetero-Diels-Alder reactions: An Efficient Asymmetric One-Pot Strategy to Isochromene Pyrimidinedione Derivatives" Organic Letters, 2012, 14, 448-451.

  • Bor-Cherng Hong,* Prakash Kotame, and Gene-Hsiang Lee, "Asymmetric Synthesis of 3,4-Dihydrocoumarin Motif with an All-Carbon         Quaternary Stereocenter via a Michael-Acetalization Sequence with Bifunctional Amine-thiourea Organocatalysts" Organic Letters, 2011, 13, 5758-5761.

  • Bor-Cherng Hong,* Nitin S. Dange, Che-Sheng Hsu, Ju-Hsiou Liao, and Gene-Hsiang Lee, "Dynamic Kinetic Asymmetric Synthesis of Five Contiguous Stereogenic Centers by Sequential Organocatalytic Stetter and Michael−Aldol Reaction: Enantioselective Synthesis of Fully Substituted Cyclopentanols Bearing a Quaternary Stereocenter" Organic Letters, 2011, 13, 1338-1341.

  • Bor-Cherng Hong,* Roshan Y. Nimje, Cheng-Wei Lin, and Ju-Hsiou Liao, "Enantioselective Organocatalytic Michael−Wittig−Michael−Michael Reaction: Dichotomous Construction of Pentasubstituted Cyclopentanecarbaldehydes and Pentasubstituted Cyclohexanecarbaldehy" Organic Letters, 2011, 13, 1278-1281.

  • Bor-Cherng Hong,* Prakash Kotame, and Ju-Hsiou Liao, " Enantioselective organocatalytic domino Michael–acetalization–Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones" Org. Biomol. Chem. 2011, 9, 382-386.

  • Bor-Cherng Hong,* Nitin S. Dange, Che-Sheng Hsu, and Ju-Hsiou Liao, "Sequential Organocatalytic Stetter and Michael–aldol Condensation Reaction: Asymmetric Synthesis of Fully Substituted Cyclopentenes via a [1 + 2 + 2] Annulation Strategy" Organic Letters, 2010, 12, 4812-4815.

  • Bor-Cherng Hong,* Prakash Kotame, Chih-Wei Tsai, and Ju-Hsiou Liao, "Enantioselective Total Synthesis of (+)-Conicol via Cascade Three-Component Organocatalysis" Organic Letters, 2010, 12, 776-779.

  • Bor-Cherng Hong,* Rei-Hau Jan, Chih-Wei Tsai, Roshan Y. Nimje, Ju-Hsiou Liao and Gene-Hsiang Lee, " Organocatalytic Enantioselective Cascade Michael-Michael-Wittig Reactions of Phosphorus Ylides: One-Pot Synthesis of the all-cis Trisubstituted Cyclohexenecarboxylates via the [1 + 2 + 3] Annulation" Organic Letters, 2009, 11, 5246-5249.

  • Bor-Cherng Hong,* Roshan Y. Nimje and Ju-Hsiou Liao, "Enantioselective synthesis of highly functionalized octahydro-6-oxo-1-phenylnaphthalene-2-carbaldehydes via organocatalytic domino reactions" Org. Biomol. Chem. 2009, 7, 3095–3101.

  • Prakash Kotame, Bor-Cherng Hong* and Ju-Hsiou Liao “Enantioselective synthesis of the tetrahydro-6H-benzo[c]chromenes via Domino Michael–Aldol condensation: control of five stereocenters in a quadruple-cascade organocatalytic multi-component reaction.” Tetrahedron Letters, 2009, 50, 704-707.

  • Hong, B. C.; Nimje, R. Y.; Sadani, A. A.; Liao, J. H. “Organocatalytic Enantioselective Domino Michael-aldol Condensation of 5-Oxoalkanal and α,β-Unsaturated Aldehydes. Efficient Assembly of Densely Functionalized Cyclohexenes” Organic Letters, 2008, 10, 2345-2348.

  • Hong, B. C.; Liu, K. L.; Tsai, C. W.; Liao, J. H. “Proline-Mediated Dimerization of Cinnamaldehydes via 1,3-Dipolar Cycloaddition Reaction with Azomethine Ylides. A Rapid Access to Highly Functionalized Hexahydro-1H-Pyrrolizine..” Tetrahedron Letters, 2008, 49, in print.

  • Hong, B. C.; Nimje, R. Y.; Wu, M. F.; Sadani, A. A. “Organocatalytic Double Michael Reaction of 7-Oxohept-2-enoates and Nitrostyrene – Formal Synthesis of (–)-α- and (–)-β-Lycorane” Eur. J. Org. Chem. 2008, 1449-1457.

  • Hong, B. C.; Wu, M. F.; Tseng, H. C.; Huang, G. F.; Su, C. F.; Liao, J. H. “Organocatalytic Asymmetric Robinson Annulation of α,β-Unsaturated Aldehydes: Applications to the Total Synthesis of (+)-Palitantin” J. Org. Chem. 2007, 72, 8459-8471.

  • Hong, B. C.; Tseng, H. C.; Chen, S. H. “Synthesis of Aromatic Aldehydes by Organocatalytic [4 + 2] and [3 + 3] Cycloaddition of α,β-Unsaturated Aldehydes” Tetrahedron, 2007, 63, 2840-2850.

  • Hong, B. C.;Yang, C.-Y.; Nimje, R. “The Organocatalytic Direct Self-Trimerization of Acrolein:  Application to the Total Synthesis of Montiporyne F.” Tetrahedron Letters, 2007, 48, 1121-1125.

  • Hong, B. C.; Nimje, R. “Catalytic C–C Bond Formation in Natural Products Synthesis: Highlights From The Years 2000– 2005” invited review, Current Organic Chemistry, 2006, 10, 2191-2225.

  • Hong, B. C.; Jiang, Y.-F.; Chang, Y.-L.; Lee, S.-J. “Synthesis and Cytotoxivity Studies of Cyclohepta[b]indoles, Benzo[6.7]cyclohepta[1,2-b]indoles, indeno[1,2-b]indoles, and Benzo[a]carbazoles.J. Chin. Chem. Soc., 2006, 53, 647-662.

  • Hong, B. C.; Wu, M.-F.; Tseng, H.-C.; Liao, J.-H. “Enantioselective Organocatalytic [3+3] Cycloaddition of α,β-Unsaturated Aldehydes and application to the Asymmetric Synthesis of (-)-Isopulegol Hydrate and (-)-Cubebaol” Organic Letters, 2006, 8, 2217-2220.

  • Hong, B. C.; Hallur, M. S.; Liao, J.-H. “Hetero Diels–Alder Cycloaddition of Indene for the Formal Synthesis of Onychnine” Synth. Commun. 2006, 36, 1521-1528.

  • Hong, B. C.; Kim, S.; Kim, T.-S.; Corey, E. J. “Synthesis and properties of several isomers of the cardioactive steroid ouabain” Tetrahedron Letters, 2006, 47, 2711-2715.

  • Tseng, H.-C.; Gupta, A. K.; Hong, B. C.; Liao, J.-H. ”Regioselective Electrophilic Substitutions of Fulvenes with Ethyl Glyoxlate and Subsequent Diels-Alder Reactions.” Tetrahedron 2006, 62, 1425-1432.

  • Chen, S.-H.; Hong, B. C.; Su, C.-F.; Sarshar, S. “An unexpected inversion of enantioselectivity in the proline catalyzed intramolecular Baylis-Hillman reaction” Tetrahedron Lett. 2005, 46, 8899-8903.

  • Hong, B. C.; Chen, Z.-Y.; Nagarajan, A.; Rudresha, K.; Chavan, V.; Chen, W.-H.; Jiang, Y.-F.; Zhang, S.-C.; Lee, G.-H.; Sarshar, S. “Efficient and Stereodivergent Synthesis of Deoxyimino Sugars” Carbohydrate Research 2005, 340, 2457-2468.

  • Hong, B. C.; Chen, F.-L.; Chen, S.-H.; Liao J.-H.; Lee, G.-H. “Intramolecular Diels-Alder Cycloadditions of Fulvenes.  Application to the Kigelinol, Neoamphilectane and Kempane Skeletons.” Organic Letters, 2005, 7, 557-560.

  • Hong, B. C.; Chen, Z.-Y.; Nagarajan, A.; Rudresha, K.; Chavan, V.; Chen, W.-H.; Jiang, Y.-F.; Zhang, S.-C.; Lee, G.-H.; Sarshar, S. “Efficient Synthesis of Enantiomerically Pure Dihydropyrans” Tetrahedron Lett. 2005, 46, 1281-1285.

  • Hong, B. C.; Chen, Z.-Y.; Chen, W.-H.; Sun, H.-I.; Lee, G.-H. “Traceless Solid-Phase Synthesis of Cyclopenta[c]quinolines and Cyclopenta[c]chromenes via Hetero [6+3] Cycloadditions of Fulvene.  A Facile Approach to the 11-heterosteroids framework.J. Chin. Chem. Soc., 2005, 52, 182-200.

  • Hong, B. C.; Wu, J.-L.; Gupta, A.; Hullar, M. S.; Liao, J.-H. “Azadiene Diels-Alder Cycloaddition of Fulvenes: A Facile Approach to the [1]Pyrindine System”, Org. Lett. 2004, 6, 3453-3456.

  • Hong, B. C.; Gupta, A. K.; Wu, M.-F.; Liao, J.-H. “Formal [6+3] Cycloaddition of Fulvenes with 2H-azirine: a Facile Approach to the [2]Pyrindines System”, Tetrahedron Lett. 2004, 45, 1663-1666.

  • Hong, B. C.; Gupta, A. K.; Wu, M.-F.; Liao, J.-H.; Lee, G.-H. “Hetero [6+3] Cycloaddition of Fulvenes with N-Alkylidene Glycine Esters: A Facile Synthesis of the Delavayine and Incarvillateine Framework”, Org. Lett. 2003, 5, 1689-1692.

  • Hong, B. C.; Shr, Y.-J.; Liao, J.-H. “Unprecedented Microwave Effects on the Cycloaddition of Fulvenes. A New Approach to the Construction of Polycyclic Ring Systems”, Org. Lett. 2002, 4, 663 -666.

  • Hong, B. C.; Shr, Y.-J.; Wu, J. L.; Gupta A. K.; Lin, K. J. “Novel [6+2] Cycloaddition of Fulvenes with Alkenes: A Facile Synthesis of the Anislactone and Hirsutane Framework”, Org. Lett. 2002, 4, 2249-2252.

  • Hong, B. C.; Shen, I. C.; Liao, J.-H. “Unprecedented Sequential Oxidative Dimerization and Cycloaddition of 1,3-Diketones to Fulvenes: A facile Synthesis of the Cyclopenta[b]chromenes”, Tetrahedron Lett. 2001, 42, 935-938.

  • B.C. Hong, Y.F. Jiang and E.S. Kumar, "Microwave-Assisted [6+4]-Cycloaddition of Fulvenes and a-Pyrones to Form Azulene-indoles. Facile Syntheses of New Antineoplastic Agents.", Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984.

  • B.C. Hong, I.C. Shen and J.H. Liao , "Unprecedented Sequential Oxidative Dimerization and Cycloaddition of 1,3-Diketones to Fulvenes: A facile Synthesis of the Cyclopenta[b]chromenes", Tetrahedron Lett. 2001, 42, 935-938.

  • B.C.Hong, H.I.Sun, Y.J.Shr and K.J.Lin, "A Novel Oxidative Alkylation-Nitration of 1,3-Dicarbonyl Compounds to Dicyclopentadiene and Norbornene", J. Chem. Soc. Perkin 1, 2000, 2939-2942.

  • B.C.Hong,Z.Y.Chen and W.H.Chen, "Traceless Solid-Phase Synthesis of Heterosteroid Framework", Organic Letters, 2000, 2, 2647-2649.

  • B.C. Hong, H.I. Sun and Z.Y. Chen, "Unprecedented and Novel Hetero [6+3] Cycloadditions of Fulvenes. A Facial Synthesis of 11-oxasteroids Frameworks", Chem. Commun., 1999, 2125-6.

  • B.C. Hong, Z.Y. Chen and E.S. Kumar "Unprecedented Oxidative Addition of alpha-halo Acyl Halide to 6,6-Dialkoxyfulvene", J. Chem. Soc. Perkin 1, 1999, 1135-7.

  • B.C. Hong and S.F. Chin, "Bicyclo[3.2.1]octanes via McMurry Couplings", Synth. Commun., 1999, 29, 3097-3106.

  • B.C. Hong and S. Sarsha, "Recent Advances in the Synthesis of Indan System. A Review", invited paper in Organic Preparations and Procedures International, 1999, 31, 1-86.

  • B.C. Hong Jang-Hsing Hong and Yann-Chien Tsai, "Regio- and Enantioselective Prenyl Anion Transfer: Application to the Total Synthesis of (-)-Rosiridol", Angew. Chem. Int. Ed. Engl., 1998, 37, 468-470.

  • B.C. Hong Si-shoung Sun and Yann-Chien Tsai, "Metal Mediated [6+3] Cycloaddition Reactions of Fulvenes. A Novel Approach to the Indan Systems", J. Org. Chem, 1997, 62, 7717-7725.