Asymmetric synthesis of the putative structure of (-)-oryzoxymycin

被引:63
作者
Bunnage, ME
Ganesh, T
Masesane, IB
Orton, D
Steel, PG
机构
[1] Univ Durham, Dept Chem, Durham DH1 3LE, England
[2] Pfizer Ltd, Global Res & Dev, Sandwich CT13 9NJ, Kent, England
关键词
D O I
10.1021/ol0269704
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A short asymmetric synthesis of (2'S,5R,6R)-2'-[6-amino-5-hydroxy-1,3-cyclohexadiene-1-carbonyloxy]propionic acid, the enantiomer of the reported structure of (+)-oryzoxymycin is described. The reported spectral data does not match that obtained for synthetic "oryzoxymycin".
引用
收藏
页码:239 / 242
页数:4
相关论文
共 26 条
[1]   ISOLATION AND STRUCTURE ELUCIDATION OF THE 4-AMINO-4-DEOXYCHORISMATE INTERMEDIATE IN THE PABA= ENZYMATIC PATHWAY [J].
ANDERSON, KS ;
KATI, WM ;
YE, CZ ;
LIU, J ;
WALSH, CT ;
BENESI, AJ ;
JOHNSON, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :3198-3200
[2]   STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES [J].
BLOCH, R ;
GUIBEJAMPEL, E ;
GIRARD, C .
TETRAHEDRON LETTERS, 1985, 26 (34) :4087-4090
[4]  
CAMPBELL MM, 1993, SYNTHESIS-STUTTGART, P179
[5]   Synthesis and X-ray crystal structure of (-)-calicheamicinone [J].
Clive, DLJ ;
Bo, YX ;
Selvakumar, N ;
McDonald, R ;
Santarsiero, BD .
TETRAHEDRON, 1999, 55 (11) :3277-3290
[6]  
Couché E, 1999, SYNLETT, P87
[7]   Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid [J].
Evans, DA ;
Barnes, DM .
TETRAHEDRON LETTERS, 1997, 38 (01) :57-58
[8]   TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN [J].
FUKUYAMA, T ;
NAKATSUKA, S ;
KISHI, Y .
TETRAHEDRON, 1981, 37 (11) :2045-2078
[9]   The chemistry of 2-aminocycloalkanecarboxylic acids [J].
Fülöp, F .
CHEMICAL REVIEWS, 2001, 101 (07) :2181-2204
[10]   ABSOLUTE STRUCTURE OF ORYZOXYMYCIN [J].
HASHIMOTO, T ;
KONDO, S ;
NAGANAWA, H ;
TAKITA, T ;
MAEDA, K ;
UMEZAWA, H .
JOURNAL OF ANTIBIOTICS, 1974, 27 (01) :86-87