Enantioselective syntheses of (2S,4aS,8aR)-1,1,4a-trimethyldecahydronaphthalen-2-ol[(-)-TMD], (4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one, and (-)-Polywood(R), through Michael-type reaction of chiral imines

被引：24

作者：

Jabin, I ^{[1
]}

Revial, G ^{[1
]}

Melloul, K ^{[1
]}

Pfau, M ^{[1
]}

机构：

[1] ECOLE SUPER PHYS & CHIM IND VILLE PARIS, CNRS URA 476, CHIM ORGAN LAB, F-75231 PARIS 05, FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(97)00082-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The title compounds 6, 15, and 17 have been synthesized in a straightforward way in good yields and high enantiomeric excesses by the chiral imines method, leading to building-blocks 2 and 10, followed by a few conventional steps. (C) 1997 Elsevier Science Ltd.

引用

页码：1101 / 1109

页数：9

共 83 条

[1] THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES UNDER NEUTRAL CONDITIONS - STEREOCHEMICAL EVIDENCES IN SUPPORT OF A CYCLIC TRANSITION-STATE [J].

AMBROISE, L ;

DESMAELE, D ;

MAHUTEAU, J ;

DANGELO, J .

TETRAHEDRON LETTERS, 1994, 35 (52) :9705-9708

[2]

[Anonymous], [No title captured]

[3] SYNTHETIC APPROACHES TO PENTACYCLIC TRITERPENES OF THE ARBORANE FAMILY [J].

ARSENIYADIS, S ;

RODRIGUEZ, R ;

CABRERA, E ;

THOMPSON, A ;

OURISSON, G .

TETRAHEDRON, 1991, 47 (34) :7045-7058

[4] SYNTHESIS OF THE INDIVIDUAL ENANTIOMERS OF THE BENZOQUINOLINONE HUMAN TYPE-1 STEROID 5-ALPHA-REDUCTASE INHIBITORS LY191704 AND LY266111 [J].

AUDIA, JE ;

LAWHORN, DE ;

DEETER, JB .

TETRAHEDRON LETTERS, 1993, 34 (44) :7001-7004

[5] ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES [J].

BARTA, NS ;

BRODE, A ;

STILLE, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6201-6206

[6] Structural and stereoelectronic requirements for the inhibition of mammalian 2,3-oxidosqualene cyclase by substituted isoquinoline derivatives [J].

Barth, MM ;

Binet, JL ;

Thomas, DM ;

deFornel, DC ;

Samreth, S ;

Schuber, FJ ;

Renaut, PP .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (12) :2302-2312

[7] FACILE ENANTIOSELECTIVE SYNTHESIS OF 2 NEW BICYCLIC CHIRAL TEMPLATES [J].

BELFIELD, KD ;

SEO, J .

SYNTHETIC COMMUNICATIONS, 1995, 25 (04) :461-466

[8] ASYMMETRIC BRIDGING ANNULATION REACTION INVOLVING THE INTRAMOLECULAR CONJUGATE ADDITION OF CHIRAL IMINES TO ENOATES - ACCESS TO A POLYCYCLIC SYSTEM RELATED TO THE TAXANE CORE [J].

CAVE, C ;

BOGGERO, S ;

CASAS, R ;

DUMAS, F ;

MAHUTEAU, J ;

DANGELO, J .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2647-2650

[9] METHYL-METHACRYLATE AS ACCEPTOR IN THE ASYMMETRIC MICHAEL REACTION USING CHIRAL BETA-ENAMINOESTERS - SIMULTANEOUS, COMPLETE STEREOCONTROL OF A QUATERNARY CARBON CENTER AND A TERTIARY ONE IN THE BETA-POSITION [J].

CAVE, C ;

DALEY, V ;

DANGELO, J ;

GUINGANT, A .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :79-82

[10] Stereochemical aspects in the asymmetric Michael addition of chiral imines to substituted electrophilic alkenes [J].

Cave, C ;

Desmaele, D ;

dAngelo, J ;

Riche, C ;

Chiaroni, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4361-4368

← 1 2 3 4 5 6 7 8 9 →