Total synthesis of cochleamycin A.
[reaction: see text] Cochleamycin A (1) was synthesized in 2.4% overall yield via a 23-step linear sequence starting from 3-butene-1-ol. Key features of the synthesis include the synthesis of (Z)-1,3-diene 21 via a Stille coupling of 4 and 5 and a transannular Diels-Alder reaction of macrocycle 26 to provide the complete carbon skeleton of 1.
Dineen
Thomas A
TA
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Roush
William R
WR
D003517:Cyclopentanes / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D008968:Molecular Conformation
D003517:Cyclopentanes; D007783:Lactones; C099300:cochleamycin A