title: Total Synthesis of (-)-Exiguolide.
abstract: A concise total synthesis of (-)-exiguolide has been completed in an overall 2.8% yield over 20 steps in the longest linear path. The key strategies involve (1) Prins cyclization/homobromination of dienyl alcohol with the B ring-substituted aldehyde, prepared by Prins cyclization/bromination, to construct the A ring with excellent cis-Z stereochemical control and (2) an unusual side chain installation/macrocyclization strategy featuring Sonogashira cross-coupling followed by a ring-closing metathesis reaction to deliver the target.
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
authors.forename: Zhigao
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
authors.forename: Hengmu
authors.initials: H
authors.lastname: Xie
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
authors.forename: Hongze
authors.initials: H
authors.lastname: Li
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
authors.forename: Lu
authors.initials: L
authors.lastname: Gao
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
authors.forename: Zhenlei
authors.initials: Z
authors.lastname: Song
mesh_terms: D000818:Animals; D002384:Catalysis; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C527475:exiguolide