Cookies on this website
We use cookies to ensure that we give you the best experience on our website. If you click 'Continue' we'll assume that you are happy to receive all cookies and you won't see this message again. Click 'Find out more' for information on how to change your cookie settings.

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