title: Total synthesis of cis-sylvaticin.
abstract: An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP 4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.
authors.affiliation: School of Chemistry, University of Southampton, Highfield, Southampton, UK.
authors.forename: Lynda J
authors.initials: LJ
authors.lastname: Brown
authors.forename: Ian B
authors.initials: IB
authors.lastname: Spurr
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Kemp
authors.forename: Nicholas P
authors.initials: NP
authors.lastname: Camp
authors.forename: Karl R
authors.initials: KR
authors.lastname: Gibson
authors.forename: Richard C D
authors.initials: RC
authors.lastname: Brown
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry*; D031045:Rollinia / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; D011090:Polyenes; C063434:sylvaticin; D015107:4-Butyrolactone