title: Asymmetric total synthesis of (+)-attenol B.
abstract: The more cytotoxic, thermodynamically less stable (+)-attenol B was isolated as a minor isomer of the spiroketal attenol A and synthesized previously as a minor product. Herein, we report a new strategy that for the first time led to asymmetric synthesis of (+)-attenol B as an exclusive product, featuring sequential Achmatowicz rearrangement/bicycloketalization to efficiently construct the 6,8-dioxabicyclo[3.2.1]octane core. In addition, (-)-attenol A was obtained with 91% yield by isomerization of (+)-attenol B in CDCl3.
authors: Department of Chemistry, The Hong Kong University of Science and Technology , Clearwater Bay, Kowloon, Hong Kong, China.
authors: Jingyun
authors: J
authors: Ren
authors: Jian
authors: J
authors: Wang
authors: Rongbiao
authors: R
authors: Tong
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049872:Bivalvia / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004988:Ethers, Cyclic; C423354:attenol A