Abstract
The first syntheses of 9-J1-phytoprostane and 9-A 1-phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47% overall yield. The two upper side-chains, with a stereodefined E double bond, were installed using consolidated Julia-Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α-protected aldehyde 6.
Original language | English |
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Pages (from-to) | 2111-2119 |
Number of pages | 9 |
Journal | European Journal of Organic Chemistry |
Volume | 2014 |
Issue number | 10 |
DOIs | |
Publication status | Published - 2014 |
Keywords
- Asymmetric synthesis
- Natural products
- Olefination
- Phytoprostanes
- Total synthesis
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry