Studies on the Enantioselective Synthesis of -Ethylidene-bearing Spiro[indolizidine-1,3'-oxindole] Alkaloids

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Jan 20

PMID 33467493

Authors

Nihan Yayik

Maria Perez

Elies Molins

Joan Bosch

Mercedes Amat

Affiliations

Soon will be listed here.

Abstract

A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3'-oxindole] framework present in a large number of oxindole alkaloids, with a H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an -ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the -ethylidene substituent by acetylation at the α-position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7()-geissoschizol oxindole has been prepared.

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