Concise Total Synthesis of Curvulone B

Abstract

A concise and convergent stereoselective synthesis of Curvulone B is described. The synthesis utilized the tandem isomerization followed by C-O and C-C bond forming reaction following Mukaiyama-type aldol conditions for the construction of trans-2,6-disubstituted dihydropyran ring system as the key step. Other important features of this synthesis are cross-metathesis, epimerization and Friedel-Crafts acylation reaction.

Mukaiyama aldol reaction: an effective asymmetric approach to access chiral natural products and their derivatives/analogues

“…They are isolated from the known sea-water algal species i.e., Gracilaria folifera. 145 Considering the utility of the curvulone type natural product, Banoth et al 146 in 2020 carried out a brief and efficient total synthesis of curvulone by utilizing the Mukaiyama aldol reaction as one of its key steps. For this purpose, homoallylalcohol 335 was reacted with acrolein and Hoveyda Grubbs II reagent in dichloromethane to obtain unsaturated aldehyde 336 in 87% yield.…”