Stereoselective synthesis of the C(1)-C(13) segment of dolabelide B.

Tetrahedron Lett

Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, UT 84112-0850, USA.

Published: July 2005

The efficient construction of the C(1)-C(13) segment of dolabelide B is described. A key element of the synthesis entails BITIP catalyzed asymmetric methallylation to establish the C(7) stereocenter, which was then used to direct the stereoselective installation of the C(9) and C(11) centers through Evans reduction and 1,5-anti aldol condensation, respectively.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1540402PMC
http://dx.doi.org/10.1016/j.tetlet.2005.04.146DOI Listing

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