Abstract
The first synthesis of (±)-tetrapetalone A-Me aglycon is described. Key bond-forming reactions include Nazarov cyclization, a ring-closing metathesis promoted with complete diastereoselectivity by a chiral molybdenum-based complex, tandem conjugate reduction/intramolecular aldol cyclization, and oxidative dearomatization.
Keywords:
cross-coupling; cyclization; metathesis; natural products; polycycles.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclization
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Glycosides / chemical synthesis*
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Glycosides / chemistry
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Molecular Conformation
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Molybdenum / chemistry
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Organometallic Compounds / chemistry
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Stereoisomerism
Substances
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Glycosides
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Heterocyclic Compounds, 4 or More Rings
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Organometallic Compounds
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tetrapetalone A
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Molybdenum