Chemistry Publications

Document Type

Article

Publication Date

10-7-2013

Journal

Tetrahedron

Volume

69

Issue

40

First Page

8632

Last Page

8644

URL with Digital Object Identifier

http://dx.doi.org/10.1016/j.tet.2013.07.026

Abstract

An allylic cis-epoxide prepared by Sharpless asymmetric epoxidation was transformed in 9 steps and 41% overall yield to the cyclization precursor 4 via a key one carbon homologation. Cobalt catalyzed aerobic oxidative cyclization of 4 gave the trans-THF in 94% yield at gram scale. Subsequent manipulations, including a Still-Gennari olefination, Sharpless asymmetric dihydroxylation, Corey-Fuchs alkynylation and Kazmaier hydrostannylation provided the fully functionalized C(1)-C(9) fragment 2 suitable for cross coupling. The sequence is readily scalable and provides gram quantities of 2


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