Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method. Issue 12 (10th March 2022)

• Record Type: Journal Article
• Authors: Chatterjee, Shrestha; Acharyya, Ranjan Kumar; Pal, Pratik; Nanda, Samik
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 12(2022)
• Page Start: 2473
• Page End: 2499
• Publication Date: 2022-03-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00166g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Visible light-induced photoisomerization method of γ-( Z )-alkylidenebutenolides to their corresponding E -components is investigated and explored further for total synthesis of related natural products. 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.