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Synthesis 2023; 55(20): 3349-3363
DOI: 10.1055/a-2105-2774
DOI: 10.1055/a-2105-2774
paper
Scalable, Stereocontrolled, Total Synthesis of Carolacton
This project received financial support from CAMS Innovation Fund for Medical Sciences (CIFMS 2016-I2M-3-009 and CIFMS 2017-I2M-3-011) and the Natural Science Foundation of China (21272279)
Abstract
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2105-2774.
- Supporting Information
Publication History
Received: 04 April 2023
Accepted after revision: 02 June 2023
Accepted Manuscript online:
02 June 2023
Article published online:
07 August 2023
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