Abstract
A completely stereocontrolled asymmetric synthesis of an advanced B-ring synthon for the bryostatin family of antitumor agents is reported. Noteworthy features of our synthesis include the Smith-Tietze bis-alkylation reaction between 12 and 13 en route to C(2)-symmetrical ketone 10 and the totally stereoselective conversion of 10 into triol 18 via a Grignard addition tactic. Triol 18 was converted to epoxide 3 in nine steps, and an acid-catalyzed intramolecular Williamson etherification reaction completed the synthesis of 2.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkenes / chemistry*
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Alkenes / metabolism
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Alkylation
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / metabolism
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Bryostatins
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Epoxy Compounds / metabolism
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Ethers / metabolism
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Humans
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Ketones / metabolism
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Lactones / chemical synthesis*
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Lactones / chemistry
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Lactones / metabolism
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Macrolides / chemical synthesis*
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Macrolides / chemistry
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Macrolides / metabolism
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Stereoisomerism
Substances
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Alkenes
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Antineoplastic Agents
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Bryostatins
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Epoxy Compounds
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Ethers
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Ketones
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Lactones
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Macrolides
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bryostatin 1