title: Total synthesis of (-)-exiguolide via an organosilane-based strategy.
abstract: An organosilane-based strategy has been used to accomplish the convergent total synthesis of (-)-exiguolide. The key steps involve: (1) geminal bis(silyl) Prins cyclization to construct the A ring; (2) silicon-protected RCM reaction to construct the 20-membered macrocycle; and (3) Hiyama-Denmark cross-coupling of vinylsilane with vinyliodide to install the triene side chain.
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China. zhenleisong@scu.edu.cn.
authors.forename: Hongze
authors.initials: H
authors.lastname: Li
authors.forename: Hengmu
authors.initials: H
authors.lastname: Xie
authors.forename: Zhigao
authors.initials: Z
authors.lastname: Zhang
authors.forename: Yongjin
authors.initials: Y
authors.lastname: Xu
authors.forename: Ji
authors.initials: J
authors.lastname: Lu
authors.forename: Lu
authors.initials: L
authors.lastname: Gao
authors.forename: Zhenlei
authors.initials: Z
authors.lastname: Song
mesh_terms: D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D018942:Macrolides; D012821:Silanes; D014753:Vinyl Compounds; C527475:exiguolide; C569210:vinyl iodide; C476909:vinylsilane