title: Total synthesis of aculeatin A via double intramolecular oxa-Michael addition of secondary/tertiary alcohols.
abstract: A new synthetic strategy was developed for a concise total synthesis of aculeatin A as a single spiroisomer in both racemic and enantioselective fashions in 8-10 steps with ∼10% overall yield from the known alkyne 11, featuring phenol oxidative dearomatization, double intramolecular oxa-Michael addition of secondary/tertiary alcohols, and chemo- and stereoselective reduction of ketone. The new synthetic strategy greatly expedites the access to the potent antiprotozoal aculeatin A, 6-epi-aculeatin D, and their analogues.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong, China.
authors.forename: Hongliang
authors.initials: H
authors.lastname: Yao
authors.forename: Liyan
authors.initials: L
authors.lastname: Song
authors.forename: Rongbiao
authors.initials: R
authors.lastname: Tong
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C436886:1,7-dioxa-dispiro(5.1.5.2)pentadeca-9,12-dien-11-one; D000438:Alcohols; D003512:Cyclohexanones; D013141:Spiro Compounds; C476177:aculeatin A