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Synlett 2012(2): 263-266  
DOI: 10.1055/s-0031-1290090
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Concise Formal Synthesis of (+)-Englerin A and Total Synthesis of (-)-Orientalol F: Establishment of the Stereochemistry of the Organocatalytic [4+3]-Cycloaddition Reaction

Chao-Lei Wanga,b, Bing-Feng Sun*a, Shu-Guang Chena,c, Rui Dinga, Guo-Qiang Lin*a, Jin-Yi Xu*b, Yong-Jia Shangc
a CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, P. R. of China
Fax: +86(21)54925081; e-Mail: bfsun@sioc.ac.cn; e-Mail: lingq@sioc.ac.cn.;
b Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, P. R. of China
e-Mail: jinyixu@china.com;
c College of Chemistry and Materials Science, Anhui Normal University, Beijing East Road No. 1, Wuhu 241000, P. R. of China
Further Information

Publication History

Received 11 October 2011
Publication Date:
05 December 2011 (online)

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Concise Formal Synthesis of (+)-Englerin A and Total Synthesis of (-)-Orientalol F: Establishment of the Stereochemistry of the Organocatalytic [4+3]-Cycloaddition ReactionSynlett 2012; 2012(08): 1266-1266
DOI: 10.1055/s-0031-1290674

Abstract

The enantioselective formal synthesis of (+)-englerin A and the total synthesis of (-)-orientalol F were successfully accomplished via a triene. The success enabled establishment of the relative as well as absolute stereochemistry of the organocatalytic [4+3]-cycloaddition reaction.

Key words

asymmetric synthesis - chemoselectivity - regioselectivity - natural product - cycloaddition

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