Enantioselective Synthesis of (+)-Peganumine A

• Published in: Journal of the American Chemical Society (ISSN: 1520-5126), vol. 138, num. 35, p. 11148-11151
• Washington: American Chemical Society, 2016

A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind−Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C−C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enantioselective Pictet−Spengler reaction followed by a transannular cyclization. This last reaction created two spirocycles and a 2,7-diazabicyclo[2.2.1]heptan-3-one unit with excellent control of both the absolute and relative stereochemistry of the two newly created quaternary stereocenters.

Reference

• EPFL-ARTICLE-221315
• doi:10.1021/jacs.6b07846
• View record in Web of Science

Record created on 2016-09-14, modified on 2017-05-12