Journal
ORGANIC LETTERS
Volume 22, Issue 9, Pages 3345-3350Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00773
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Funding
- NSERC
- NSERC/Servier Senior Industrial Research Chair program
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For the first time, we describe the stereocontrolled total syntheses of olivil, cephafortin A, 4-des-O-methyl-4-O-rhamnosyl cephafortin A, and alashinol F from a common precursor using a combination of chemoenzymatic and biomimetic methods for the systematic introduction of functional groups on three vicinal stereogenic carbon atoms. We revised the previously assigned stereochemistry of (+)-cephafortin A, which was reported as the enantiomer. Natural and unnatural congeners provide insights into the biogenetic interrelations of members of this family.
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