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Molecules 2013, 18(7), 8243-8256; doi:10.3390/molecules18078243
Article

Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations

*  and
Department of Chemistry, Fu Jen Catholic University, New Taipei City 24205, Taiwan
* Author to whom correspondence should be addressed.
Received: 16 May 2013 / Revised: 2 July 2013 / Accepted: 3 July 2013 / Published: 12 July 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

Starting from a thio-substituted 4-quinolizidinone, a series of C-6 alkylated derivatives with a trans C-6, C-9a relationship was synthesized. Further transformations led to the first stereoselective total synthesis of the structure proposed for (±)-quinolizidine 195C, the major alkaloid isolated from the skin extracts of the Madagascan frog Mantella betsileo. Since the spectral data of the synthetic and natural products differed significantly, the true structure of (±)-quinolizidine 195C remains uncertain.
Keywords: aza-Diels-Alder reaction; intramolecular aza-Michael reaction; quinolizidines; quinolizidine 195C aza-Diels-Alder reaction; intramolecular aza-Michael reaction; quinolizidines; quinolizidine 195C
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Chou, S.-S.P.; Huang, J.-L. Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations. Molecules 2013, 18, 8243-8256.

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