title: A synthetic approach for constructing the 3/6/6/5-fused tetracyclic skeleton of tenuipesine A.
abstract: An efficient approach toward the 3/6/6/5-fused tetracyclic skeleton of tenuipesine A has been accomplished. The strategy featured 1) a tandem Mitsunobu and 3,3-rearrangement reaction yielding the key intermediate 7 with two adjacent all-carbon quaternary centers with high d.r.; and 2) a tandem DBDMH-mediated semipinacol rearrangement via a 1,2-oxygen migration of an allylic hemiketal to construct the highly substituted tetrahydropyran ring.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 (P. R. China).
authors.forename: Jin-Miao
authors.initials: JM
authors.lastname: Tian
authors.forename: Xiong
authors.initials: X
authors.lastname: Zhao
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Wei
authors.initials: W
authors.lastname: Gong
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Wang
mesh_terms: D008968:Molecular Conformation; D013237:Stereoisomerism; D014255:Trichothecenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D014255:Trichothecenes; C507167:tenuipesine A
keywords: Mitsunobu reaction; rearrangement; semipinacol; synthesis; tenuipesine A