Synthesis of the Acyclic Carbon Skeleton of Filipin III

• DOI: 10.1021/acs.joc.6b01166
• Publication Date: 2016-08-09T15:18:48Z
• Authors: Elodie Brun; Véronique Bellosta; Janine Cossy
• Keywords: Stereocenter; Carbon skeleton; Polyene; Sequence (biology)

The synthesis of the carbon skeleton filipin III, a polyenic macrolactone possessing 11 stereogenic centers, was achieved using convergent strategy with longest linear sequence 19 steps starting from hexanal. Construction polyene realized two successive Heck couplings as key steps. Control centers polyol fragment performed by utilizing an Evans aldolization, 1,3-syn enantio- and diastereoselective allylations, hemiacetalization/oxa-Michael sequence, reduction. fragments were coupled 1,5-anti aldolization followed 1,3-anti