A concise total synthesis of amphidinolide T2.
RCM + AD = T2: In the presence of the C16-methylene group, regioselective ring-closing metathesis (RCM) formed the (12E)-endocyclic double bond, which underwent Os-catalyzed asymmetric dihydroxylation (AD) to give the desired 12,13-diol intermediate required for the total synthesis of amphidinolide T2 in 16 linear steps in 8.0% overall yield.
Li
Huoming
H
Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
Wu
Jinlong
J
Luo
Jialu
J
Dai
Wei-Min
WM
D002384:Catalysis; D006900:Hydroxylation; D007773:Lactates / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D008024:Ligands; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000097442:Amphidinolides
D007773:Lactates; D007783:Lactones; D008024:Ligands; D018942:Macrolides; C578435:amphidinolide T2; D000097442:Amphidinolides; C028444:methyl lactate