Gram scale synthesis of the C(18)-C(34) fragment of amphidinolide C.

Authors

Nicholas A Morra
Brian L Pagenkopf

Document Type

Article

Publication Date

2-18-2011

Journal

Organic letters

Volume

13

Issue

4

First Page

572

Last Page

575

URL with Digital Object Identifier

10.1021/ol1030074

Abstract

The synthesis of the C(18)-C(34) fragment of amphidinolide C has been achieved via two routes, culminating in both the shortest (11 steps) and highest yielding (26% overall yield) approaches to this segment. The highly convergent approach will facilitate the synthesis of analogues, including the C(18)-C(29) fragment of amphidinolide F. Synthetic highlights include the selective methylation of a diyne, and the highly efficient use of a second generation cobalt catalyst in the Mukaiyama oxidative cyclization to form the trans-THF ring.