Asymmetric Synthesis of (-)-Martinellic Acid

作者:Davies Stephen G*; Fletcher Ai M; Lee James A; Lorkin Thomas J A; Roberts Paul M; Thomson James E
来源:Organic Letters, 2013, 15(8): 2050-2053.
DOI:10.1021/ol4007508

摘要

A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(alpha-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant beta-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture.

  • 出版日期2013-4-19