Control of olefin geometry in the bryostatin B-ring through exploitation of a C-2-symmetry breaking tactic and a Smith- Tietze coupling reaction.
[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
|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
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
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