Issue 26, 2011
From the journal:

Chemical Communications

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

Hisataka Kobayashi,a   Makoto Kanematsu,a   Masahiro Yoshidaa  and  Kozo Shishido*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan
E-mail: shishido@ph.tokushima-u.ac.jp
Fax: +81 88-633-9575
Tel: +81 88-633-7287

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.

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

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Article information

DOI
https://doi.org/10.1039/C1CC12114F
Article type
Communication
Submitted
13 Apr 2011
Accepted
16 May 2011
First published
31 May 2011

Chem. Commun., 2011,47, 7440-7442

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

H. Kobayashi, M. Kanematsu, M. Yoshida and K. Shishido, Chem. Commun., 2011, 47, 7440 DOI: 10.1039/C1CC12114F

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