A Divergent Enantioselective Synthesis of 9-J(1)-Phytoprostane and 9-A(1)-Phytoprostane Methyl Ester

作者:Porta Alessio*; Chiesa Francesco; Quaroni Marco; Persico Marco; Moratti Remigio; Zanoni Giuseppe; Vidari Giovanni
来源:European Journal of Organic Chemistry, 2014, 2014(10): 2111-2119.
DOI:10.1002/ejoc.201301703

摘要

The first syntheses of 9-J(1)-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 -protected aldehyde 6.

  • 出版日期2014-4