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

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

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-δ-lactone, Dötz benzannulation...

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Veröffentlicht in:Journal of organic chemistry 2012-11, Vol.77 (22), p.10455-10460
Hauptverfasser: Fernandes, Rodney A, Chavan, Vijay P, Mulay, Sandip V, Manchoju, Amarender
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Molecular Structure
Naphthoquinones - chemical synthesis
Naphthoquinones - chemistry
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
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Zusammenfassung: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-δ-lactone, Dötz benzannulation, oxa-Pictet-Spengler reaction, and H2SO4-mediated epimerization.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3019939