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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.

Original publication

DOI

10.1021/ol4007508

Type

Journal article

Journal

Org Lett

Publication Date

19/04/2013

Volume

15

Pages

2050 - 2053

Keywords

Alkylation, Amides, Crystallography, X-Ray, Esters, Lithium, Molecular Conformation, Molecular Structure, Pyrroles, Quinolines, Stereoisomerism, Trifluoroacetic Acid