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
