Consecutive alkene cross-metathesis/oxonium ylide formation-rearrangement: synthesis of the anti-HIV agent hyperolactone C.
Alpha-diazo-beta-ketoesters bearing allylic ether functionality undergo highly stereoselective Ru-carbene-catalyzed alkene cross-metathesis followed by Rh(2)(OAc)(4)-catalyzed oxonium ylide formation/[2,3] sigmatropic rearrangement in a one-flask operation and in a highly diastereoselective manner. The methodology has been demonstrated in a concise synthesis of the anti-HIV agent hyperolactone C.
Hodgson
David M
DM
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
Angrish
Deepshikha
D
Erickson
Stephanie P
SP
Kloesges
Johannes
J
Lee
Caroline H
CH
D000475:Alkenes / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure
D000475:Alkenes; D019380:Anti-HIV Agents; D005663:Furans; C488315:hyperolactone C