Abstract
The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N 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.
Original language | English |
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Pages (from-to) | 3287-3291 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 22 |
Issue number | 10 |
DOIs | |
Publication status | Published - Mar 1 2016 |
Externally published | Yes |
Keywords
- Enders RMAP
- Grieco-Nishizawa olefination
- Keck allylation
- Shi-epoxidation
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry