title: Stereoselective synthesis of the C5-C18 fragment of halichomycin.
abstract: An efficient and convergent synthesis of the C(5)-C(18) fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C(5)-C(18) fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
authors.forename: Qingjiang
authors.initials: Q
authors.lastname: Li
authors.forename: Shiyong
authors.initials: S
authors.lastname: Mao
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Cui
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
mesh_terms: D000478:Alkylation; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; C454439:halichomycin