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ChemInform Abstract: Synthesis of the C19 Through C27 Segment of Okadaic Acid Using Vinylogous Urethane Aldol Chemistry. Part 3.

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

Publisher: John Wiley and Sons
Year: 2010
Weight: 41 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199842250

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✦ Synopsis

Synthesis of the C 19 Through C 27 Segment of Okadaic Acid Using Vinylogous Urethane Aldol Chemistry. Part 3.

-The approach towards the C 19 -C 27 fragment (X) of okadaic acid is accomplished employing a highly enantio-and diastereoselective aldol coupling reaction of the chiral vinylogous urethane lactone enolate (I). The remainder of the carbon skeleton of this segment is constructed by the diastereoselective γ-oxygenated addition of the allylstannane (VI). Formation of the tetrahydropyran ring is achieved utilizing a stereoselective electrophilic cyclization. -(DANKWARDT,

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