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DOI: 10.1055/a-1477-6043
Wittig Reactions of Maleimide-Derived Stabilized Ylides with Alkyl Pyruvates: Concise Approach to Methyl Ester of (±)-Chaetogline A
N.P.A. thanks Science and Engineering Research Board (SERB), New Delhi, for financial support.
Abstract
A facile synthesis of methyl ester of chaetogline A is reported starting from the corresponding methyl 1-methyltryptophanate-derived maleimide. A stereoselective Wittig olefination with a carbonyl function in methyl pyruvate followed by phosphorous pentoxide-induced regioselective dehydrative cyclization are the essential reactions. An acid-induced thermodynamically driven stereoselective β- to α-position migration of the exocyclic C=C bond unit in ethyl tetrahydroindolizinoindolylidenepropanoate is described.
Key words
natural product - chaetogline A - amino acid - maleimide - methyl pyruvate - Wittig reaction - dehydrative cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1477-6043.
- Supporting Information
Publication History
Received: 09 March 2021
Accepted after revision: 08 April 2021
Accepted Manuscript online:
08 April 2021
Article published online:
03 May 2021
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