Progress toward the total synthesis of bafilomycin A(1): stereoselective synthesis of the C15-C25 subunit by additions of nonracemic allenylzinc reagents to aldehydes.
[reaction: see text] A highly stereoselective synthesis of the C15-C25 subunit (2) of bafilomycin A(1) (1) has been accomplished by a route utilizing additions of chiral nonracemic allenylzinc reagents to aldehydes.
Marshall
J A
JA
Department of Chemistry, McCormick Road, P.O. Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Adams
N D
ND
D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D018942:Macrolides; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000447:Aldehydes; D000466:Alkadienes; D000900:Anti-Bacterial Agents; D018942:Macrolides; D009942:Organometallic Compounds; C025947:propadiene; C040929:bafilomycin A1; D015032:Zinc