Synthetic studies on amphidinolide B1.
[structure: see text]. The syntheses of three fragments, 2, 3, and 4, of amphidinolide B1 have been accomplished. The 1,3-isomerization of allylic alcohol 10 was accomplished via rhenium oxo catalysis and has been applied successfully in the synthesis. (-)-MIB-catalyzed asymmetric vinylzinc addition to aldehyde 31 and the regio- and stereoselective epoxidation of unsymmetrical divinyl methanol 32 were key steps.
Mandal
Amit K
AK
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8103, USA.
Schneekloth
John S
JS
Kuramochi
Kouji
K
Crews
Craig M
CM
D000818:Animals; D002384:Catalysis; D004141:Dinoflagellida / Q000737:chemistry; D007202:Indicators and Reagents; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
D007202:Indicators and Reagents; D018942:Macrolides; C511225:amphidinolide B1; D000097442:Amphidinolides