Tetrahedron p. 9509 - 9524 (1997)
Update date:2022-07-29
Topics:
Nara, Shinji
Toshima, Hiroaki
Ichihara, Akitami
Asymmetric total synthesis of (+)-coronafacic acid (2), was accomplished via intramolecular 1, 6-conjugate addition as the key step. The chiral ester (+)-7 was prepared via two approaches: starting from (R)-(+)-4-acetoxy-2- cyclopenten-1-one (12), and using catalytic asymmetric Michael reactions promoted by heterobimetallic BINOL complexes. Coupling between (+)-2 and the protected coronamic acid 8 and subsequent deprotection by hydrogenolysis provided (+)-coronatine (1). This is the first asymmetric total synthesis of(+)-1.
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