SYNTHESIS OF CONDURITOL-A, CONDURITOL-(+)-C AND CONDURITOL-(-)-C FROM D-GALACTOSE

被引：14

作者：

MEREYALA, HB

GADDAM, BR

机构：

[1] Bio-Organic Laboratory, Indian Institute of Chemical Technology

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 15期

关键词：

D O I：

10.1039/p19940002187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach for the stereoselective synthesis of conduritols A 1, (+)-C 3 and (-)-C 3 starting from D-galactose is described. The utility of the key cyclohexenone intermediate 11 leading to the synthesis of conduritols 1, (+)-3 and (-)-3 by straightforward synthetic manipulations is described.

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页码：2187 / 2190

页数：4

相关论文

共 33 条

[1] PROTON MAGNETIC RESONANCE SPECTRA AND CONFORMATIONS OF CYCLIC COMPOUNDS .2. PMR SPECTRA OF CONDURITOLS [J].

ABRAHAM, RJ ;

GOTTSCHA.H ;

PAULSEN, H ;

THOMAS, WA .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (NOV) :6268-&

[2] CONDURITOLS AND RELATED-COMPOUNDS [J].

BALCI, M ;

SUTBEYAZ, Y ;

SECEN, H .

TETRAHEDRON, 1990, 46 (11) :3715-3742

[3] FUNCTIONALIZED CARBOCYCLES FROM CARBOHYDRATES .8. UNSATURATED CARBOHYDRATES .28. OBSERVATIONS ON THE CONVERSION OF 6-DEOXYHEX-5-ENOPYRANOSYL COMPOUNDS INTO 2-DEOXYINOSOSE DERIVATIVES [J].

BLATTNER, R ;

FERRIER, RJ ;

HAINES, SR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2413-2416

[4] ENANTIOSPECIFIC SYNTHESIS OF (4S,5S,6S)-4,5,6-TRIHYDROXYCYCLOHEX-2-ENONE AND (+)-CONDURITOL-C FROM FLUOROBENZENE VIA MICROBIAL OXIDATION [J].

CARLESS, HAJ ;

OAK, OZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (02) :61-62

[5] ENANTIOSPECIFIC AND STEREOSELECTIVE SYNTHESIS OF (-)-CONDURITOL-C FROM CHLOROBENZENE VIA MICROBIAL OXIDATION AND EPOXIDATION [J].

CARLESS, HAJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :234-235

[6] TOTAL SYNTHESIS OF ANTIBIOTIC HYGROMYCIN-A [J].

CHIDA, N ;

OHTSUKA, M ;

NAKAZAWA, K ;

OGAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2976-2983

[7]

DANGSCHAT G, 1939, NATURWISSENSCHAFTEN, V27, P756

[8]

DUMORTIER L, 1992, SYNLETT, P243

[9] COMPLEX STEREOCHEMICAL COURSE OF THE MITSUNOBU INVERSION OF ALLYLIC ALCOHOLS [J].

FARINA, V .

TETRAHEDRON LETTERS, 1989, 30 (48) :6645-6648

[10] UNSATURATED CARBOHYDRATES .21. CARBOCYCLIC RING-CLOSURE OF A HEX-5-ENOPYRANOSIDE DERIVATIVE [J].

FERRIER, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1455-1458

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