Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.
[reaction: see text] The synthesis of the C9-C26 portion of amphidinolide B1 is described. A Fleming allylation followed by elimination was employed for the construction of the C13-C15 diene portion. Sharpless asymmetric dihydroxylation was utilized for regioselective functionalization of a styrene-derived alkene, in the presence of the C13-C15 diene functionality. A highly diastereoselective aldol reaction was developed to establish the C18 stereochemistry.
Zhang
Wei
W
Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, Oregon 97331, USA.
Carter
Rich G
RG
D002244:Carbon / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000097442:Amphidinolides
D002244:Carbon; D018942:Macrolides; C511225:amphidinolide B1; D000097442:Amphidinolides