Abstract
Stereocontrolled access to the hexacyclic core of FD-594 has been achieved. The key steps include the intramolecular S(N)Ar reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI(2)-mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antibiotics, Antineoplastic / chemical synthesis*
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Antibiotics, Antineoplastic / chemistry
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Lactones / chemical synthesis*
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Lactones / chemistry
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Pyrans / chemical synthesis*
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Pyrans / chemistry
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Stereoisomerism
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Streptomyces / chemistry
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Streptomyces / metabolism
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Xanthenes / chemical synthesis*
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Xanthenes / chemistry
Substances
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Antibiotics, Antineoplastic
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FD 594, antibiotic
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Lactones
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Pyrans
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Xanthenes