ITERATIVE DIASTEREOSELECTIVE REDUCTION OF HYDROXY DIKETOESTERS TO ALL 1,3,5 SYN TRIOLS - SYNTHESIS OF C1-C10 FRAGMENT OF NYSTATIN A1

被引：14

作者：

BONINI, C ^{[1
]}

RIGHI, G ^{[1
]}

ROSSI, L ^{[1
]}

机构：

[1] UNIV LA SAPIENZA,DIPARTIMENTO CHIM,CTR STUDIO CHIM SOSTANZE NAT,CNR,I-00185 ROME,ITALY

来源：

TETRAHEDRON | 1992年 / 48卷 / 44期

关键词：

D O I：

10.1016/S0040-4020(01)81196-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

the iterative diastereoselective reduction of a model hydroxy 3,5 diketo ester to the corresponding skipped 1,3,5 triol ester was studied in different conditions. The use of NaBH4/Ti(OiPr)4 in THF leads with good stereoselection to the syn-syn triol ester as the main product; the described method has been applied to an extremely short synthesis of the C1-C10 fragment (in racemic form) of the macrolide antibiotic Nystatin A1.

引用

页码：9801 / 9808

页数：8

共 15 条

[1] CONVENIENT SYNTHESIS OF TRIACETIC ACID METHYL-ESTER [J].

BATELAAN, JG .

SYNTHETIC COMMUNICATIONS, 1976, 6 (02) :81-83

[2] STUDIES ON ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY-DELTA-LACTONE INHIBITORS OF HMGCOA REDUCTASE .1. A NEW PREPARATION OF THE LACTONE MOIETY OF COMPACTIN [J].

BONADIES, F ;

DIFABIO, R ;

GUBBIOTTI, A ;

MECOZZI, S ;

BONINI, C .

TETRAHEDRON LETTERS, 1987, 28 (06) :703-706

[3]

BONINI C, 1991, GAZZ CHIM ITAL, V121, P75

[4] A NOVEL METHOD FOR THE INSITU GENERATION OF ALKOXYDIALKYLBORANES AND THEIR USE IN THE SELECTIVE PREPARATION OF 1,3-SYN DIOLS [J].

CHEN, KM ;

GUNDERSON, KG ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

CHEMISTRY LETTERS, 1987, (10) :1923-1926

[5] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[6] THE DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING ME4NHB(OAC)3 [J].

EVANS, DA ;

CHAPMAN, KT .

TETRAHEDRON LETTERS, 1986, 27 (49) :5939-5942

[7] REDUCTION OF BETA-HYDROXY KETONES WITH CATECHOLBORANE - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF SYN 1,3-DIOLS [J].

EVANS, DA ;

HOVEYDA, AH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5190-5192

[8] A FACILE ENTRY TO BETA,DELTA-DIKETO AND SYN-BETA,DELTA-DIHYDROXY ESTERS [J].

HANAMOTO, T ;

HIYAMA, T .

TETRAHEDRON LETTERS, 1988, 29 (49) :6467-6470

[9]

HAZEN EL, 1950, SCIENCE, V112, P423

[10] COMPLETE STEREOSTRUCTURE OF NYSTATIN-A1 - A PROTON NMR-STUDY [J].

LANCELIN, JM ;

BEAU, JM .

TETRAHEDRON LETTERS, 1989, 30 (34) :4521-4524

← 1 2 →