Issue 11, 2005
From the journal:

Organic & Biomolecular Chemistry

Total syntheses of enantiomerically enriched R-(+)- and S-(−)-deplancheine†

Nadiya Sydorenko,a   Craig A. Zificsak,a   Aleksey I. Gerasyutoa  and  Richard P. Hsung*a  

* Corresponding authors

a Department of Chemistry, University of Minnesota, Minneapolis, MN 55455
E-mail: hsung@chem.umn.edu

Abstract

Total syntheses of indoloquinolizidine alkaloid (±)-, R-(+)-, and S-(−)-deplancheine are described here. The synthesis features an enantioselective intramolecular formal aza-[3 + 3] cycloaddition for the construction of the quinolizidine CD-ring. This application serves to introduce a new synthetic strategy for the synthesis of indoloquinolizidine alkaloids.

Graphical abstract: Total syntheses of enantiomerically enriched R-(+)- and S-(−)-deplancheine

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Article information

DOI
https://doi.org/10.1039/B503862F
Article type
Paper
Submitted
16 Mar 2005
Accepted
14 Apr 2005
First published
25 Apr 2005

Org. Biomol. Chem., 2005,3, 2140-2144

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Total syntheses of enantiomerically enriched R-(+)- and S-(−)-deplancheine

N. Sydorenko, C. A. Zificsak, A. I. Gerasyuto and R. P. Hsung, Org. Biomol. Chem., 2005, 3, 2140 DOI: 10.1039/B503862F

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