A Versatile Enantioselective Synthesis of Azabicyclic Ring Systems: a Concise Total Synthesis of (+)-grandisine D and Unnatural Analogues

Overview

Journal Chemistry

Specialty Chemistry

Date 2012 Apr 5

PMID 22473565

Citations 8

Authors

Olugbeminiyi O Fadeyi

Timothy J Senter

Kristopher N Hahn

Craig W Lindsley

Affiliations

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Abstract

Closing in on azacines: We have developed a new six step approach for the rapid and enantioselective synthesis of indolizidine, pyrrolo[1,2-a]azepine, and pyrrolo[1,2-a]azocine azabicyclic systems and their respective lactam congeners, which are found in a host of natural products as well as pharmaceutical preparations. This protocol enables a concise enantioselective total synthesis of (+)-grandisine D in 16.4 % overall yield from commercial materials (see scheme).

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