Issue 12, 2022

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

Abstract

A general and flexible visible light-induced photoisomerization method of γ-(Z)-alkylidenebutenolides to their corresponding E-components was reported in this article. Initially, a series of naturally occurring enantiopure γ-(Z)-alkylidenebutenolides was synthesized by employing a “Pd–Cu” bimetallic cascade cyclization protocol. In the later part, the synthesized γ-(Z)-alkylidenebutenolides were photoisomerized in the presence of a triplet photosensitizer to γ-(E)-alkylidenebutenolides in reasonably acceptable yields. Total synthesis of goniobutenolides, hygrophorones, ramariolide D, melodorinols/acetyl-melodorinols, versicolactones, and phomopsolidones was achieved by employing the developed methods.

Graphical abstract: Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

Supplementary files

Article information

Article type
Paper
Submitted
26 Jan 2022
Accepted
01 Mar 2022
First published
01 Mar 2022

Org. Biomol. Chem., 2022,20, 2473-2499

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

S. Chatterjee, R. K. Acharyya, P. Pal and S. Nanda, Org. Biomol. Chem., 2022, 20, 2473 DOI: 10.1039/D2OB00166G

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