title: Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers.
abstract: The syntheses of members of a family of lindenane sesquiterpenoid [4+2] dimers led to the total syntheses of sarcandrolide J and shizukaol D. Inspired by a modified biosynthetic pathway, a cascade featuring furan formation/alkene isomerization/Diels-Alder cycloaddition was devised to construct the congested polycyclic architecture of the target molecules with the correct stereochemistry. This study presents a pioneering synthetic entry to this family of natural products and paves the way for fully exploring their biological functions.
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Rd., Chengdu, Sichuan, 610064, China.
authors.forename: Changchun
authors.initials: C
authors.lastname: Yuan
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Rd., Chengdu, Sichuan, 610064, China.
authors.forename: Biao
authors.initials: B
authors.lastname: Du
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Rd., Chengdu, Sichuan, 610064, China.
authors.forename: Heping
authors.initials: H
authors.lastname: Deng
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Rd., Chengdu, Sichuan, 610064, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Man
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Rd., Chengdu, Sichuan, 610064, China.|State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, China.
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
mesh_terms: D061565:Cycloaddition Reaction; D019281:Dimerization; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D012717:Sesquiterpenes; D014315:Triterpenes; C587032:shizukaol D
keywords: biomimetic synthesis; cycloaddition; natural products; terpenoids; total synthesis