Efficient access to a dihydropyran-containing macrolide via a transannular oxy-Michael reaction: total synthesis of (+)-aspergillide C

Hisataka Kobayashi; Makoto Kanematsu; Masahiro Yoshida; Kozo Shishido

doi:10.1039/c1cc12114f

Efficient access to a dihydropyran-containing macrolide via a transannular oxy-Michael reaction: total synthesis of (+)-aspergillide C

Chem Commun (Camb). 2011 Jul 14;47(26):7440-2. doi: 10.1039/c1cc12114f. Epub 2011 May 31.

Authors

Hisataka Kobayashi¹, Makoto Kanematsu, Masahiro Yoshida, Kozo Shishido

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan.

PMID: 21629897
DOI: 10.1039/c1cc12114f

Abstract

The second-generation enantioselective total synthesis of aspergillide C, a new type of 14-membered macrolide isolated from a marine-derived fungus, has been accomplished in a longest linear sequence of 15 steps from a chiral building block in 19% overall yield employing the 6-exo-trig transannular oxy-Michael reaction as the key step.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Macrolides / chemical synthesis*
Macrolides / chemistry*
Pyrans / chemistry*
Stereoisomerism

Substances

Macrolides
Pyrans
aspergillide C