☆ 4.7 Article

A Chiron Approach to the Total Synthesis of (-)-Juglomycin A, (+)-Kalafungin, (+)-Frenolicin B, and (+)-Deoxyfrenolicin

JOURNAL OF ORGANIC CHEMISTRY (2012)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 77, 期 22, 页码 10455-10460

出版社

AMER CHEMICAL SOC

DOI: 10.1021/jo3019939

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Chemistry, Organic

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Department of Science and Technology, New Delhi [SR/S1/OC-25/2008]
Council of Scientific and Industrial Research (CSIR) New Delhi

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摘要

A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, D-glucono-delta-lactone, Dotz benzannulation, oxa-Pictet-Spengler reaction, and H2SO4-mediated epimerization.

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