Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 14, Pages 5643-5654Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050664x
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By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group.
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