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A practical synthesis of the F-ring of halichondrin B via ozonolytic desymmetrization of a C(2)-symmetric dihydroxycyclohexene.
Jiang, Lei; Martinelli, Joseph R; Burke, Steven D.
Affiliation
  • Jiang L; Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
J Org Chem ; 68(3): 1150-3, 2003 Feb 07.
Article in En | MEDLINE | ID: mdl-12558449
C(2)-symmetric dihydroxycyclohexene 1 was desymmetrized via a one-pot Criegee ozonolysis/acylation protocol to afford acetal-lactone 2. Installation of the allyl side chain on the convex face of the bicyclic system and subsequent reduction provided the desired tetrahydrofuran 4 with the correct relative and absolute stereochemistries. Simple functional group manipulations led to the desired F-ring module 3 of halichondrin B.
Subject(s)
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Collection: 01-internacional Database: MEDLINE Main subject: Ethers, Cyclic / Antineoplastic Agents Language: En Journal: J Org Chem Year: 2003 Document type: Article Affiliation country: United States Country of publication: United States
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Collection: 01-internacional Database: MEDLINE Main subject: Ethers, Cyclic / Antineoplastic Agents Language: En Journal: J Org Chem Year: 2003 Document type: Article Affiliation country: United States Country of publication: United States