Scalable, Stereocontrolled, Total Synthesis of Carolacton

Synthesis DOI: 10.1055/a-2105-2774 A route for the scalable, stereocontrolled, total synthesis of carolacton is presented starting from commercially available S-Roche ester, d-ribose, and a known allylic alcohol. Key transformations in the total synthesis include a [3,3]-Claisen rearrangement, Sharpless asymmetric epoxidation–methyl ring-opening, or Leighton asymmetric crotylation, Evans aldol–reductive deoxygenation, and ring closing metathesis (RCM). The total synthesis of carolacton (151 mg isolated, 9.2% overall yield) was completed in 23 linear steps. Additionally, 56 mg of the carolacton C15–C16 cis-olefin isomer was obtained. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - August 7, 2023 Category: Chemistry Authors: Bian, Chuan-Cai Li, Yong-Qiang Yang, Hao-ran Yu, Xiao-Ming Tags: paper Source Type: research