Issue 10, 1992
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Short enantioselective approach to heteroyohimbine alkaloids from meso-bicyclo[3.3.0]octane-3,7-dione: synthesis of methyl 2-epielenolate

John Leonard,   Dehimi Quali  and  Shirley K. Rahman  

Abstract

meso-Bicyclo[3.3.0]octane-3,7-dione mono ethylene ketal 1 has been converted into chiral enol derivatives with good enantioselectivity. In this paper we report the efficient stereoselective transformation of meso-bicyclo[3.3.0]octane-3,7-dione mono ethylene ketal into methyl 2-epielenolate 15, a direct precursor to the heteroyohimbine alkaloid tetrahydroalstonine. The synthetic work described shows that each ring of the bicyclic ketone can be functionalized independently with good regio- and stereo-control. A new procedure for installing the alkoxyacrylate function of mono-terpenoids is described and it has been shown that the cyclopentanone ring of methyl (1αH,6αH)-2α-methyl-8-oxo-3-oxabicyclo[4.3.0]non-4-ene-5--carboxylate 11 can be regiosalectively converted into enol derivatives which are cleaved to give D/E-ring precursors of Corynanthé alkaloids.

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Article information

DOI
https://doi.org/10.1039/P19920001203
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 1203-1207

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Short enantioselective approach to heteroyohimbine alkaloids from meso-bicyclo[3.3.0]octane-3,7-dione: synthesis of methyl 2-epielenolate

J. Leonard, D. Quali and S. K. Rahman, J. Chem. Soc., Perkin Trans. 1, 1992, 1203 DOI: 10.1039/P19920001203

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