Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 5, Pages 2414-2435Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02838
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Funding
- Council of Scientific and Industrial Research, New Delhi, India
- DST
- Department of Science and Technology of India [SB/S5/GC-03/2013, EMR/2016/000988]
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A convergent and flexible strategy for the stereoselective total synthesis of the reported structure of baulamycin A and its congeners has been developed for the first time. Synthetic highlights include a Crimmins aldol reaction to construct the C-1' and C-14 centers, a Crimmins acetate aldol reaction to generate the hydroxy group at the C-13 position, Horner-Wadsworth-Emmons olefination to form the C-9-C-10 bond, and Evans methylation to install the C-8 center. This synthetic study disclosed that the reported structure of baulamycin A needs to be revised, as its spectroscopic data are not identical with those of the synthetic baulamycin A.
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