Linear and convergent polypropionate chain synthesis via oxiranes

ORGN 687

Jose A. Prieto, japrieto@uprrp.edu1, Wildeliz Torres, wildeliz@hotmail.com2, Marlenne Mulero, mulero_m@yahoo.com2, and Wilnelia Dávila, wilnie@hotmail.com2. (1) Department of Chemistry, University of Puerto Rico at Rio Piedras Campus, PO Box 23346, San Juan, PR 00931-3346, (2) Department of Chemistry, University of Puerto Rico, PO Box 23346, San Juan, PR 00931-3346
Alternating hydroxyl and methyl groups on an aliphatic chain with a distinct stereochemistry is known as a polypropionate unit, which is a common feature of many macrolides and ionophores, including the ansamycin and plecomacrolide family of antibiotics. In our laboratory, we have been developing a general stereoselective synthetic strategy to polypropionates based on oxirane chemistry. We have undertaken a study on the reaction of alkynyl alanes and alkenyl Grignard reagents with 2,3- and 3,4-epoxy alcohols. We have observed high regioselectivity in the cleavage of these systems where the preferred side of the attack depends on the stereochemical disposition of the substituents and/or the organometallic reagent used. We have applied this methodology to the synthesis of the polypropionate chains of streptovaricin D and bafilomycin A1. Supported by NIH RISE (1R25-GM-61151-01A1) and NIH SCORE (2S06-GM-008102)

 

New Reactions and Methodology
1:00 PM-5:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

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