title: Stereoselective synthesis of the C(25)-C(36) segment of arenicolides A and B: determination of the configuration of the trisubstituted epoxide.
abstract: Two diastereomeric epoxides 4a and 4b corresponding to the C(25)-C(36) fragment of arenicolides A and B were synthesized in a stereoselective manner involving the Pd(0)-catalyzed stereospecific methoxy substitution reaction of epoxy unsaturated ester 6 with B(OMe)(3) as the key step. Comparison of the (1)H NMR spectra of the synthetic compounds with that of arenicolide A revealed that the configuration of the epoxide in arenicolides A and B is 30R and 31R.
authors.affiliation: Department of Applied Chemistry, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.
authors.forename: Shinji
authors.initials: S
authors.lastname: Nagumo
authors.forename: Taeko
authors.initials: T
authors.lastname: Nakano
authors.forename: Kyomi
authors.initials: K
authors.lastname: Hata
authors.forename: Megumi
authors.initials: M
authors.lastname: Mizukami
authors.forename: Masaaki
authors.initials: M
authors.lastname: Miyashita
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D004852:Epoxy Compounds; D018942:Macrolides; C521798:arenicolide A; C521799:arenicolide B