Stereoselective synthesis of the C(25)-C(36) segment of arenicolides A and B: determination of the configuration of the trisubstituted epoxide.
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.
Nagumo
Shinji
S
Department of Applied Chemistry, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.
Nakano
Taeko
T
Hata
Kyomi
K
Mizukami
Megumi
M
Miyashita
Masaaki
M
D004852:Epoxy Compounds / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D004852:Epoxy Compounds; D018942:Macrolides; C521798:arenicolide A; C521799:arenicolide B