title: Synthesis of each enantiomer of rocaglamide by means of a palladium(0)-catalyzed Nazarov-type cyclization.
abstract: A recently reported Pd(0)-catalyzed asymmetric Nazarov-type cyclization has been successfully applied in the key step of the first catalytic asymmetric total synthesis of (-)-rocaglamide (natural) and (+)-rocaglamide. The stereochemistry at the C3 position that controls the stereochemistry of all other stereocenters is determined in the cyclization step. This versatile and modular synthesis proceeds from simple reagents.
authors.affiliation: Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA).
authors.forename: Zhe
authors.initials: Z
authors.lastname: Zhou
authors.forename: Marcus A
authors.initials: MA
authors.lastname: Tius
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D010165:Palladium; C107772:rocaglamide
keywords: cyclization; enantiomers; natural products; palladium; total synthesis