Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol

被引:54
作者
Trost, BM [1 ]
Hembre, EJ [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1016/S0040-4039(98)02274-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically pure (+)-cyclophellitol is readily available from benzoquinone employing an asymmetric palladium catalyzed kinetic resolution of racemic conduritol B and a novel easily cleavable pivalate analogue. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:219 / 222
页数:4
相关论文
共 23 条
[1]   SYNTHESIS OF (-)-CONDURITOL F, (+)-CONDURITOL-B, CYCLOPHELLITOL FROM L-QUEBRACHITOL [J].
AKIYAMA, T ;
SHIMA, H ;
OHNARI, M ;
OKAZAKI, T ;
OZAKI, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (12) :3760-3767
[2]   PRODUCTION, ISOLATION AND STRUCTURE DETERMINATION OF A NOVEL BETA-GLUCOSIDASE INHIBITOR, CYCLOPHELLITOL, FROM PHELLINUS SP [J].
ATSUMI, S ;
UMEZAWA, K ;
IINUMA, H ;
NAGANAWA, H ;
NAKAMURA, H ;
IITAKA, Y ;
TAKEUCHI, T .
JOURNAL OF ANTIBIOTICS, 1990, 43 (01) :49-53
[3]  
AUGYDOREY S, 1993, CHEM COMMUN, P960
[4]   Pinacol-type rearrangements of intramolecular photocycloadducts: Application of the 2,2-dimethyl-4-pentenoate protecting group [J].
Crimmins, MT ;
Carroll, CA ;
Wells, AJ .
TETRAHEDRON LETTERS, 1998, 39 (39) :7005-7008
[5]   IMPROVED PREPARATION OF (+/-)-(1,3/2,4)-5-CYCLOHEXENE-1,2,3,4-TETROL [(+/-)-CONDURITOL-B] AND ITS REACTION WITH HYDROBROMIC AND HYDROCHLORIC-ACID - SYNTHESIS AND CHARACTERIZATION OF SOME (+/-)-1,4-DIDEOXY-1-HALO-CONDURITOL AND (+/-)-1,4-DIDEOXY-1,4-DIHALO-CONDURITOL [J].
GUO, ZX ;
HAINES, AH ;
PYKE, SM ;
PYKE, SG ;
TAYLOR, RJK .
CARBOHYDRATE RESEARCH, 1994, 264 (01) :147-153
[6]   Dispiroketals in synthesis .23. A new route to (+)-D-conduritol B from myo-inositol [J].
Innes, JE ;
Edwards, PJ ;
Ley, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (06) :795-796
[7]   TOTAL SYNTHESIS OF CYCLOPHELLITOL AND (1R,2S)-CYCLOPHELLITOL FROM D-MANNOSE [J].
JUNG, ME ;
CHOE, SWT .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3280-3281
[8]   ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .11. TOTAL SYNTHESES OF (-)-CONDURITOL-B ((-)-1L-CYCLOHEX-5-ENE-1,3/2,4-TETROL) AND OF (+)-CONDURITOL-F ((+)-1D-CYCLOHEX-5-ENE-1,2,4/3-TETROL) - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF (+)-LEUCANTHEMITOL [J].
LEDRIAN, C ;
VIONNET, JP ;
VOGEL, P .
HELVETICA CHIMICA ACTA, 1990, 73 (01) :161-168
[9]  
Letellier P, 1997, SYNTHESIS-STUTTGART, P925
[10]   A DIVERGENT ROUTE FOR A TOTAL SYNTHESIS OF CYCLOPHELLITOL AND EPICYCLOPHELLITOL FROM A [2.2.2]OXABICYCLIC GLYCOSIDE PREPARED FROM D-GLUCAL [J].
MCDEVITT, RE ;
FRASERREID, B .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3250-3252