Total synthesis and structural revision of (+)-amphidinolide W.
An enantioselective first total syntheis of amphidinolide W (2) and a revision of its C6 absolute stereochemistry (1) are described. Amphidinolide W (1), a 12-membered macrolide isolated from Amphidinium sp., has shown potent antitumor properties against a variety of NCI tumor cell lines. The synthesis is convergent, and four of the five chiral centers were derived through asymmetric synthesis. The synthesis features Sharpless asymmetric dihydroxylation, diastereoselective alkylation, efficient cross metathesis of functionalized substrates, and novel functional group transformations using selective lipase-catalyzed hydrolysis of the primary acetate group. Of particular note, the C6 absolute stereochemistry of amphidinolide W (1) has now been revised through our current synthesis.
Ghosh
Arun K
AK
Department of Chemistry, University of Illinois at Chicago, 60607, USA. arunghos@uic.edu
Gong
Gangli
G
D000818:Animals; D002236:Carbohydrate Conformation; D004141:Dinoflagellida / Q000378:metabolism; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
D018942:Macrolides; C449925:amphidinolide W; D000097442:Amphidinolides