[Discodermolide: Design, total synthesis, and evaluation of c(13)-c(14) cyclopropane analogues of (+)-discodermolide]
>>Org Lett. 2005 Oct 13;7(21):4613-6.
Design, total synthesis, and evaluation of c(13)-c(14) cyclopropane analogues of (+)-discodermolide.
Smith AB 3rd, Xian M, Liu F.
Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, and Kosan Bioscience, Inc., 3832 Bay Center Place, Hayward, California 94545.
The design, total synthesis, and biological evaluation of two C(13)-C(14)-cyclopropyl analogues [(+)-1 and (+)-2] of (+)-discodermolide have been achieved. Key features of the syntheses include highly stereoselective, hydroxyl-directed cyclopropanations of vinyl iodides and higher order cuprate-mediated cross-coupling reactions between cyclopropyl iodides and alkyl iodides. Biological evaluation revealed that neither orientation of the cyclopropyl methylene completely substitutes for the C(14) methyl found in (+)-discodermolide (3).<<
Looks as though they are still feeling their way around in this program, trying to find a worthy lead.
Cheers, Tuck |
