Wittig Reactions of Maleimide-Derived Stabilized Ylides with Alkyl Pyruvates: Concise Approach to Methyl Ester of (±)-Chaetogline A

Santosh V. Shelar; Narshinha P. Argade

doi:10.1055/a-1477-6043

Synthesis, Table of Contents

Synthesis 2021; 53(16): 2897-2902
DOI: 10.1055/a-1477-6043

paper

Wittig Reactions of Maleimide-Derived Stabilized Ylides with Alkyl Pyruvates: Concise Approach to Methyl Ester of (±)-Chaetogline A

Santosh V. Shelar

^aDivision of Organic Chemistry, National Chemical Laboratory (CSIR), Pune, 411 008, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

,

Narshinha P. Argade ∗

^aDivision of Organic Chemistry, National Chemical Laboratory (CSIR), Pune, 411 008, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

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Abstract

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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 cyclization

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References

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