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Scientific article
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Short, Enantiogenic Syntheses of (-)-Indolizidine 167B and (+)-Monomorine

Published inJournal of the American Chemical Society, vol. 113, no. 9, p. 3513-3518
Publication date1991
Abstract

The enantiogenic syntheses of (-)-indolizidine 167B (1) and (+)-monomorine (2) are described. D-Norvaline and L-alanine are converted into their 1-pyrrole derivatives by reaction with 2,5-dimethoxytetrahydrofuran. Thereafter, Arndt-Eistert homologation of the N-alkanoic acid substituent, followed by rhodium(II) acetate catalyzed decomposition of its α-diazo ketone derivative, provides the relevant bicyclic precursors, the vested chirality of which directs catalytic hydrogenation affording 1 and 2. Provision for the 5-butyl side chain in 2 is made by prior Lewis acid catalyzed rearrangement of the mixed anhydride obtained from butyryl chloride and the pyrrole analogue of L-alanine.

Funding
  • Swiss National Science Foundation - 20-27'966.89
Citation (ISO format)
JEFFORD, Charles, TANG, Qian, ZASLONA, Alexander Tadeusz. Short, Enantiogenic Syntheses of (-)-Indolizidine 167B and (+)-Monomorine. In: Journal of the American Chemical Society, 1991, vol. 113, n° 9, p. 3513–3518. doi: 10.1021/ja00009a043
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ISSN of the journal0002-7863
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