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Control of olefin geometry in the bryostatin B-ring through exploitation of a C-2-symmetry breaking tactic and a Smith- Tietze coupling reaction

Hale, KJ; Hummersone, MG; Bhatia, GS; (2000) Control of olefin geometry in the bryostatin B-ring through exploitation of a C-2-symmetry breaking tactic and a Smith- Tietze coupling reaction. Organic Letters , 2 (15) 2189 - 2192.

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Abstract

[GRAPHICS] A completely stereocontrolled asymmetric synthesis of an advanced a-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

Type:Article
Title:Control of olefin geometry in the bryostatin B-ring through exploitation of a C-2-symmetry breaking tactic and a Smith- Tietze coupling reaction
Additional information:Journal Article JUL 27 337FH Hale KJ Univ Coll London, Dept Chem, Christopher Ingold Labs, 20 Gordon St, London WC1H 0AJ, England ORG LETT
Keywords:AGENTS, ANALOGS, ASYMMETRIC- SYNTHESIS, C-1-C-9, C-17-C-27 FRAGMENT, C1-C9 SEGMENT, CONSTRUCTION, control, CONVERSION, DOUBLE-BOND FORMATION, families, family, FEATURES, Geometry, PHASE-I, synthesis, SYNTHONS, VINYL RADICAL CYCLIZATION
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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