Studies aimed at the total synthesis of the antitumor antibiotic cochleamycin A. An enantioselective biosynthesis-based pathway to the AB bicyclic core.
[reaction: see text] A convergent, highly enantioselective synthesis of the fully functionalized AB sector of cochleamycin A is described. A pair of building blocks, crafted from L-malic and L-ascorbic acids, are conjoined in a manner that gives rise to an (E,Z,E)-1,6,8-nonatriene. On heating, the latter undergoes stereocontrolled intramolecular Diels-Alder cyclization via an endo transition state.
Chang
Jiyoung
J
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
Paquette
Leo A
LA
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D001205:Ascorbic Acid / Q000737:chemistry; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D008293:Malates / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry; D013237:Stereoisomerism
D000903:Antibiotics, Antineoplastic; D003517:Cyclopentanes; D007783:Lactones; D008293:Malates; D011090:Polyenes; C099300:cochleamycin A; C030298:malic acid; D001205:Ascorbic Acid