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Synthesis of the C19 through C27 segment of okadaic acid using vinylogous urethane aldol chemistry: Part III

โœ Scribed by John W. Dankwardt; Sharon M. Dankwardt; Richard H. Schlessinger


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
282 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The synthesis of the C-19 through C-27 segment of the marine natural product okadaic acid was accomplished employing a highly enantio-and diasteroselective aldol coupling reaction of a chiral vinylogous urethane lactone enolate. The remainder of the carbon skeleton of this segment was constructed by a diastereoselective y-oxygenated allylstannane addition. Formation of the tetrahydropyran ring was achieved utilizing a stereoselective electrophilic cyclization.


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