Total synthesis of (5R,6R,8R,9S)-(−)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl β-amino ketones

Franklin A. Davis; Minsoo Song; Hui Qiu; Jing Chai

doi:10.1039/B915796D

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Organic & Biomolecular Chemistry

Issue 24, 2009

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Total synthesis of (5R,6R,8R,9S)-(−)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl β-amino ketones

Franklin A. Davis , Minsoo Song , Hui Qiu and Jing Chai

Org. Biomol. Chem., 2009, 7, 5067-5073

DOI: 10.1039/B915796D
Received 03 Aug 2009, Accepted 23 Sep 2009
First published on the web 26 Oct 2009

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The first total asymmetric synthesis of the poison frog alkaloid (−)-221T, a 5,6,8-trisubstituted indolizidine is described. The key core piperidine ring was constructed via an acid catalyzed intramolecular cascade Mannich cyclization reaction of a N-sulfinyl syn-α-methyl β-amino ketone and crotonaldehyde. The β-amino ketone was prepared via the reaction of prochiral lithium Weinreb amide enolate with an enantiopure N-2,4,6-triisopropylphenylsulfinyl imine.

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¹H and ¹³C NMR data for all new compounds
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Organic & Biomolecular Chemistry

Total synthesis of (5R,6R,8R,9S)-(−)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl β-amino ketones

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