Advances and Setbacks in the Total Synthesis of the Fungal Metabolite Curvicollide C: Synthesis and Elaboration of Non-Aldol Stereotriads from Gosteli-Type Allyl Vinyl Ethers

Abstract

Advances and setbacks are reported in regard to the asymmetric total synthesis of the fungal metabolite curvicollide C relying on a synthetic strategy that exploits non-aldol stereotriads as chiral building blocks. A catalytic asymmetric Gosteli–Claisen rearrangement, a two-step aldehyde-to-alkyne-homologation, and a Julia–Kocienski olefination served as key C/C-connecting transformations.

Key words

antifungal agents - total synthesis - Claisen rearrangement - Michael addition - chiral auxiliaries - ozonolysis

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