title: Efficient enantioselective total synthesis of (-)-horsfiline.
abstract: A new efficient and concise enantioselective synthetic method for (-)-horsfiline is reported. (-)-Horsfiline could be obtained from diphenylmethyl tert-butyl malonate in 9 steps (32%,>99% ee) by using the enantioselective phase-transfer catalytic allylation (91% ee) as the key step. This approach can be applied as a practical route for the large-scale synthesis of spirooxindole natural products, which enables a systematic investigation of their biological activity to be performed.
authors.affiliation: Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
authors.forename: Suckchang
authors.initials: S
authors.lastname: Hong
authors.forename: Myunggi
authors.initials: M
authors.lastname: Jung
authors.forename: Yohan
authors.initials: Y
authors.lastname: Park
authors.forename: Min Woo
authors.initials: MW
authors.lastname: Ha
authors.forename: Cheonhyoung
authors.initials: C
authors.lastname: Park
authors.forename: Myungmo
authors.initials: M
authors.lastname: Lee
authors.forename: Hyeung-geun
authors.initials: HG
authors.lastname: Park
mesh_terms: D000478:Alkylation; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D008314:Malonates; D013141:Spiro Compounds; C443722:horsfiline
keywords: allylation; enantioselectivity; horsfiline; synthetic methods; total synthesis