A total synthesis of (+)-Goniodiol using an anomeric oxygen-to-carbon rearrangement

被引:38
作者
Dixon, DJ [1 ]
Ley, SV [1 ]
Tate, EW [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 19期
关键词
D O I
10.1039/a806584e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new route to (+)-Goniodiol 1, a potent and selective cytotoxin, is described, using a diastereoselective oxygen-to-carbon rearrangement of an anomerically linked silyl enol ether as the key step.
引用
收藏
页码:3125 / 3126
页数:2
相关论文
共 15 条
[1]   PREPARATION OF 2-EXOMETHYLENE PENAM AND PENICILLIN-2-CARBOXYLATE SYSTEMS [J].
BALDWIN, JE ;
FORREST, AK ;
KO, S ;
SHEPPARD, LN .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (02) :81-83
[2]  
Buffet MF, 1997, SYNLETT, P1055
[3]  
BUFFET MF, IN PRESS SYNLETT
[4]  
DIXON DJ, IN PRESS SYNLETT
[5]   2 NEW STYRYL LACTONES, 9-DEOXYGONIOPYPYRONE AND 7-EPI-GONIOFUFURONE, FROM GONIOTHALAMUS-GIGANTEUS [J].
FANG, XP ;
ANDERSON, JE ;
CHANG, CJ ;
MCLAUGHLIN, JL ;
FANWICK, PE .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :1034-1043
[6]  
HUANG SL, 1978, SYNTHESIS-STUTTGART, P297
[7]   ASYMMETRIC-SYNTHESIS AND BIOLOGICAL EVALUATION OF BETA-L-(2R,5S)-1,3-OXATHIOLANE AND ALPHA-L-(2R,5R)-1,3-OXATHIOLANE PYRIMIDINE AND PURINE NUCLEOSIDES AS POTENTIAL ANTI-HIV AGENTS [J].
JEONG, LS ;
SCHINAZI, RF ;
BEACH, JW ;
KIM, HO ;
NAMPALLI, S ;
SHANMUGANATHAN, K ;
ALVES, AJ ;
MCMILLAN, A ;
CHU, CK ;
MATHIS, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (02) :181-195
[8]  
LEY SV, 1994, SYNTHESIS-STUTTGART, P639
[9]   Stereoselective syntheses of (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone [J].
Mukai, C ;
Hirai, S ;
Hanaoka, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6619-6626
[10]   N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].
NAHM, S ;
WEINREB, SM .
TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818