title: Synthesis of Rings DEF of Solanoeclepin A.
abstract: An improved synthesis of rings DEF of solanoeclepin A has been achieved from ent-Hajos Parrish ketone. A key tricyclo[5.3.2.01,6]decene intermediate having an additional vinyl group as a precursor of a hydroxyl functionality was synthesized, in which the key steps included (i) a [2,3]-Wittig rearrangement to provide trans-hydroindene with C11(R)-configuration, (ii) the introduction of a vinyl group as a masked OH at C6, (iii) an oxymercurative aldol to synthesize the tricyclo[5.3.2.01,6]decene moiety, (iv) an oxidative C-C bond cleavage to yield an aldehyde and an unsaturated methyl ketone, and (v) a radical cyclization for the cyclobutane ring formation to provide the tricyclo[5.2.1.01,6]decene compound.
authors.affiliation: National Tsing Hua University , Hsinchu 300, Taiwan.
authors.forename: Hsiang-Yu
authors.initials: HY
authors.lastname: Chuang
authors.affiliation: National Tsing Hua University , Hsinchu 300, Taiwan.
authors.forename: Minoru
authors.identifier: 0000-0002-5244-3300
authors.initials: M
authors.lastname: Isobe
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006586:Hexanes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D001952:Bridged-Ring Compounds; D006586:Hexanes; C431673:solanoeclepin A