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

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

Department of Chemistry, Fu Jen Catholic University, New Taipei City 24205, Taiwan
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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. View Full-Text
Keywords: aza-Diels-Alder reaction; intramolecular aza-Michael reaction; quinolizidines; quinolizidine 195C aza-Diels-Alder reaction; intramolecular aza-Michael reaction; quinolizidines; quinolizidine 195C
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MDPI and ACS Style

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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