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ChemInform Abstract: A Vinylogous Urethane Approach Towards the Synthesis of Okadaic Acid. Construction of the C9—C18 Fragment. Part 2.

✍ Scribed by S. M. DANKWARDT; J. W. DANKWARDT; R. H. SCHLESSINGER

Publisher
John Wiley and Sons
Year
2010
Weight
39 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

A Vinylogous Urethane Approach Towards the Synthesis of Okadaic Acid. Construction of the C 9 -C 18 Fragment. Part 2.

-In the approach towards the C 9 to C 18 fragment (XI), a diastereo-and enantioselective acylation-reduction sequence of a vinylogous urethane lactone silylketene acetal sets the initial stereocenter. The remainder of the stereocenters are installed via a silyl cuprate conjugate addition trapping sequence, and transformation to the tetrahydrofuran (X). The latter is opened to give the desired olefinic alcohol utilizing dimethyl boron bromide. -(DANKWARDT, S. M.; DANKWARDT,

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