Issue 10, 2019

Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

Abstract

A stereodivergent and diastereoselective transition-metal-catalyzed intramolecular hydroamidation of allenes and alkynes furnishing δ-vinyl-lactams is reported. Employing a rhodium catalyst allowed for the selective synthesis of the syn-δ-lactam. Conversely, a palladium catalyst led to the formation of the anti-δ-lactam in high selectivity. The new method shows high functional group compatibility and assorted synthetic transformations were demonstrated as well as its utility for the enantioselective formal total syntheses of (−)-cermizine C and (−)-senepodine G.

Graphical abstract: Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Dec 2018
Accepted
24 Jan 2019
First published
24 Jan 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 3074-3079

Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

J. P. Schmidt and B. Breit, Chem. Sci., 2019, 10, 3074 DOI: 10.1039/C8SC05502E

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