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Concise Total Synthesis of (+)-Crocacin C

✍ Scribed by Sirasani, Gopal; Paul, Tapas; Andrade, Rodrigo B.

Book ID: 125532287
Publisher: American Chemical Society
Year: 2008
Tongue: English
Weight: 290 KB
Volume: 73
Category: Article
ISSN: 0022-3263
DOI: 10.1021/jo800906p

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Total synthesis of (+)-crocacin C

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The first synthesis of ( +)-crocacin C (3) in optically pure form is achieved following a convergent strategy. The synthesis also establishes the absolute stereochemistries of this novel class of potent antifungal and highly cytotoxic compounds. The naturally occurring crocacin C has (6S,7S,8R,9S) c

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Total synthesis of the potent antifungal and cytotoxic agent (+)-crocacin A is described. The crucial (Z)-5,6-enoic amide moiety in this molecule was built by stereoselective partial reduction of a skipped diyne precursor. The diene, thus obtained, was transformed into a silyl epoxide that was regio