ol4007508_si_002.pdf (688.06 kB)
Download file

Asymmetric Synthesis of (−)-Martinellic Acid

Download (688.06 kB)
journal contribution
posted on 19.04.2013, 00:00 by Stephen G. Davies, Ai M. Fletcher, James A. Lee, Thomas J. A. Lorkin, Paul M. Roberts, James E. Thomson
A high-yielding total asymmetric synthesis of (−)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3-[2′-(N,N-diallylamino)-5′-bromophenyl]propenoate and alkylation of the resultant β-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.