Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4

Abstract

Rhodium and osmium catalysed C–C and C–O bond formation under mild conditions.

Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential Catalysis

“…Recently, oxidative rearrangement reactions of homoallylic alcohols represent a new and practical strategy for the synthesis of 2,8-DOBCO derivatives. In order to construct the CDE ring fragment of PTX-4, Brimble and Donohoe, independently, designed I as new precursor of 2,8-DOBCOs (Scheme a). Triggered by epoxidation or dihydroxylation, I underwent the facile oxidative rearrangement reaction to produce targeted product.…”