First synthesis of(±)-10β-hydroxy-13β-methylcyclohexa [a]quinolizidine.: A convenient route to the ABC-part of 8-azasteroids.

被引：7

作者：

Célanire, S ^{[1
]}

Salliot-Maire, I ^{[1
]}

Ribéreau, P ^{[1
]}

Godard, A ^{[1
]}

Quéguiner, G ^{[1
]}

机构：

[1] INSA, Lab Chim Organ Fine & Heterocycl, IRCOF, UPRESA CNRS 6014, F-76131 Mt St Aignan, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 30期

关键词：

D O I：

10.1016/S0040-4020(99)00497-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of racemic 10 beta-hydroxy-13 beta-methylcyclohexa[a]quinolizidine is reported. Original construction of AC-bicyclic system is achieved by lateral metallation of 2-ethylpyridine followed by a Robinson annelation, with the creation of a quaternary picolinic carbon center. Functionalization of the A-ring and construction of the B-ring by a stereocontrolled reduction of the pyridinium salt and final hydrogenations afford the ABC-part of an 8-azasteroid. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：9269 / 9282

页数：14

共 59 条

[1] ENZYMATIC CYCLIZATION OF SQUALENE AND OXIDOSQUALENE TO STEROLS AND TRITERPENES [J].

ABE, I ;

ROHMER, M ;

PRESTWICH, GD .

CHEMICAL REVIEWS, 1993, 93 (06) :2189-2206

[2]

ABRAHAM J, 1992, INDIAN J CHEM B, V31, P566

[3] A NOVEL STEREOSPECIFIC REARRANGEMENT OF 3-SUBSTITUTED B-HOMO 5-AZASTEROIDS TO THEIR A-NOR ANALOGS - PREPARATION, STEREOCHEMISTRY, AND CONFORMATIONAL STUDIES [J].

BACK, TG ;

CHAU, JHL ;

CODDING, PW ;

GLADSTONE, PL ;

JONES, DH ;

MORZYCKI, JW ;

ROSZAK, AW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4110-4121

[4] 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

[5] PARTIAL SYNTHESIS OF THE STEROIDIC CHROMOPHORE 14A-AZA-D-HOMO-8,14A-DIENE PRESENT IN THE ANTIBIOTIC A-25822-B [J].

BARTON, DHR ;

LUSINCHI, X ;

MENENDEZ, AM ;

MILLIET, P .

TETRAHEDRON, 1983, 39 (13) :2201-2205

[6]

BEUMEL OF, 1974, SYNTHESIS-STUTTGART, P43

[7] STUDY OF SOME SIMPLE QUINOLIZINIUM DERIVATIVES [J].

BOEKELHEIDE, V ;

KAEMPFEN, HX ;

FRITZ, H ;

ROSS, JM .

TETRAHEDRON, 1964, 20 (01) :33-&

[8] LUPINEN-ALKALOIDE .8. ZUR KONFIGURATIONSBESTIMMUNG VON CHINOLIZIDIN-DERIVATEN [J].

BOHLMANN, F .

CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (10) :2157-2167

[9] 3-BETA-HYDROXY-DELTA-5-STEROID DEHYDROGENASE/3-KETO-DELTA-5-STEROID ISOMERASE FROM BOVINE ADRENALS - MECHANISM OF INHIBITION BY 3-OXO-4-AZA STEROIDS AND KINETIC MECHANISM OF THE DEHYDROGENASE [J].

BRANDT, M ;

LEVY, MA .

BIOCHEMISTRY, 1989, 28 (01) :140-148

[10] 8-AZASTEROIDS .3. 8-AZAESTROGENS AND 8-AZA-19-NORANDROGENS [J].

BROWN, RE ;

LUSTGART.DM ;

STANABAC.RJ ;

MELTZER, RI .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (05) :1489-&

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