Natural product synthesis via the oxidation of furan derivatives

ORGN 913

Dan Woollaston, Department of Chemistry, University of Oxford, 12 Mansfield Rd, Oxford, OX1 3TA, United Kingdom and Jeremy Robertson, Department of Chemistry, Oxford University, 12 Mansfield Rd, Oxford, OX1 3TA, United Kingdom.
The oxidation of 2-(ω-hydroxyalkyl)furans leads to [5,5] and [6,5] butenolide spiroacetals. We report progress towards the enantioselective syntheses of a selection of highly oxygenated biologically active natural products: Sawaranospirolides A-D, Pyrenolide D, and AL-(1). Enantioselectivity is achieved using Sharpless' catalytic dihydroxylations, and other key reactions include a one-pot furan oxidation, alkene epoxidation and epoxide opening, and a ‘halogen dance' which is used to assemble a brominated furan precursor.

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 134, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006