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A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine?D and unnatural analogues.

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).

SUBMITTER: Fadeyi OO 

PROVIDER: S-EPMC3540812 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues.

Fadeyi Olugbeminiyi O OO   Senter Timothy J TJ   Hahn Kristopher N KN   Lindsley Craig W CW  

Chemistry (Weinheim an der Bergstrasse, Germany) 20120330 19

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). ...[more]

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