title: Novel "protecting group-dependent" alkylation-RCM strategy to medium-sized oxacycles: first total synthesis of --isoprelaurefucin.
abstract: [reaction: see text] A novel "protecting group-dependent" alkylation strategy was developed for complementary diastereoselective syntheses of alpha,alpha'-syn- and alpha,alpha'-anti-bis-alkenes 2 and 3, which represent ring-closing metathesis (RCM) substrates for medium-sized oxacycles. This principle has been applied to a stereoselective and concise total synthesis of (-)-isoprelaurefucin (4) in 14 steps in 12% overall yield from known epoxide 8.
authors.affiliation: College of Pharmacy, Seoul National University, Kwanak-Ku, Korea.
authors.forename: Hyunjoo
authors.initials: H
authors.lastname: Lee
authors.forename: Hyoungsu
authors.initials: H
authors.lastname: Kim
authors.forename: Taehyun
authors.initials: T
authors.lastname: Yoon
authors.forename: Byungsook
authors.initials: B
authors.lastname: Kim
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Hee-Doo
authors.initials: HD
authors.lastname: Kim
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D000577:Amides / Q000737:chemistry; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000475:Alkenes; D000577:Amides; D006574:Heterocyclic Compounds, 2-Ring; D010082:Oxepins; C510882:isoprelaurefucin