Wittig Reactions of Maleimide-Derived Stabilized Ylides with Alkyl Pyruvates: Concise Approach to Methyl Ester of (±)-Chaetogline A-Reference-Cited by-同舟云学术

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

Published:2021-04-08 Issue:16 Volume:53 Page:2897-2902
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Argade Narshinha P.¹²^ORCID,Shelar Santosh V.¹²

Affiliation:

1. Division of Organic Chemistry, National Chemical Laboratory (CSIR)

2. Academy of Scientific and Innovative Research (AcSIR)

Abstract

AbstractA 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.

Funder

Science and Engineering Research Board

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1477-6043.pdf

Reference20 articles.

1. Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety

2. Occurrence, Biogenesis, and Synthesis of Biologically Active Carbazole Alkaloids

3. Marine Indole Alkaloids

4. Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

5. Pictet–Spengler reaction-based biosynthetic machinery in fungi