ASYMMETRIC-SYNTHESIS OF (S)-ZEARALENONE DIMETHYL ETHER, AN ORSELLINIC ACID TYPE MACROLIDE

被引：46

作者：

SOLLADIE, G ^{[1
]}

MAESTRO, MC ^{[1
]}

RUBIO, A ^{[1
]}

PEDREGAL, C ^{[1
]}

CARRENO, MC ^{[1
]}

RUANO, JLG ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM CI,E-28049 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期

关键词：

D O I：

10.1021/jo00007a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (S)-zearalenone dimethyl ether is described. The chiral part of the molecule was obtained by asymmetric synthesis monitored by a chiral sulfoxide group and introduced in the very last steps of the synthesis.

引用

页码：2317 / 2322

页数：6

共 20 条

[1] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].

CARRENO, MC ;

RUANO, JLG ;

MARTIN, AM ;

PEDREGAL, C ;

RODRIGUEZ, JH ;

RUBIO, A ;

SANCHEZ, J ;

SOLLADIE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128

[2] NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION .2. [J].

GAREGG, PJ ;

SAMUELSSON, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2866-2869

[3] SYNTHESIS OF MACROCYCLES VIA ALLYLIC RADICAL INTERMEDIATES - A TOTAL SYNTHESIS OF (-)-ZEARALENONE [J].

HITCHCOCK, SA ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1990, 31 (25) :3641-3644

[4] TOTAL SYNTHESIS OF MACROLIDE, (R,S)-ZEARALANONE [J].

HURD, RN ;

SHAH, DH .

JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (05) :543-545

[5] SYNTHESIS OF A LARGE-RING KETONE CONTAINING A LACTONE FUNCTION - DIECKMANN CONDENSATION VS THORPE-ZIEGLER CONDENSATION [J].

HURD, RN ;

SHAH, DH .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (02) :390-394

[6]

KAITO T, 1982, J ORG CHEM, V47, P1612

[7] ESTROGENIC METABOLITE PRODUCED BY FUSARIUM GRAMINEARUM IN STORED CORN [J].

MIROCHA, CJ ;

CHRISTENSEN, CM ;

NELSON, GH .

APPLIED MICROBIOLOGY, 1967, 15 (03) :497-+

[8]

RAO AVR, 1987, TETRAHEDRON, V43, P779

[9] REDUCTION OF BETA-KETO SULFOXIDES - A HIGHLY EFFICIENT ASYMMETRIC-SYNTHESIS OF BOTH ENANTIOMERS OF ALLYLIC ALCOHOLS [J].

SOLLADIE, G ;

DEMAILLY, G ;

GRECK, C .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1552-1554

[10] REDUCTION OF CHIRAL BETA-HYDROXY SULFOXIDES - APPLICATION TO THE SYNTHESIS OF BOTH ENANTIOMERS OF 4-SUBSTITUTED BUTENOLIDES [J].

SOLLADIE, G ;

FRECHOU, C ;

DEMAILLY, G ;

GRECK, C .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1912-1914

← 1 2 →