Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 10, Pages 3287-3291Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504675
Keywords
Enders RMAP; Grieco-Nishizawa olefination; Keck allylation; Shi-epoxidation; total synthesis
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The total synthesis of 7,10-epimer of the proposed structure of amphidinolideN was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP linchpin as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.
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