A concise total synthesis of (+)-scholarisine a empowered by a unique C-H arylation

Myles W. Smith; Scott A. Snyder

doi:10.1021/ja406546k

A concise total synthesis of (+)-scholarisine a empowered by a unique C-H arylation

Myles W. Smith, Scott A. Snyder

Research output: Contribution to journal › Article › peer-review

97 Scopus citations

Abstract

The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.

Original language	English (US)
Pages (from-to)	12964-12967
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	35
DOIs	https://doi.org/10.1021/ja406546k
State	Published - Sep 4 2013
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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A concise total synthesis of (+)-scholarisine a empowered by a unique C-H arylation

Abstract

ASJC Scopus subject areas

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