A NEW ROUTE TO PRECURSORS OF ECDYSTEROIDS USING A REGIOSELECTIVE AND STEREOSELECTIVE HYDROBORATION

被引：7

作者：

DOLLE, F

HETRU, C

LUU, B

机构：

[1] CNRS,CHIM ORGAN SUBSTANCES NAT LAB,5 RUE BLAISE PASCAL,F-67084 STRASBOURG,FRANCE

[2] CNRS,BIOL GEN LAB,F-67000 STRASBOURG,FRANCE

来源：

TETRAHEDRON | 1991年 / 47卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(01)96160-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a new route to precursors of ecdysteroids, using a regio- and stereoselective hydroboration. Hydroboration of 3,3-(ethylenedioxy)-cholesta-5,7-diene (from 7-dehydrocholesterol in two steps), followed by oxidation with alkaline hydrogen peroxide, produces 3,3-(ethylenedioxy)-5-beta-cholest-7-en-6-beta-ol (the same reaction with 7-dehydrocholesterol leads only to the 5-alpha-alcohol (OH-6-alpha), prohibiting the synthesis of 5-beta-steroids).

引用

收藏

页码：7059 / 7066

页数：8

相关论文

共 24 条

[11] SYNTHESIS OF PUTATIVE PRECURSORS OF ECDYSONE .3. SYNTHESIS OF 3-BETA,14-ALPHA,25-TRIHYDROXY-5-BETA-CHOLEST-7-EN-6-ONE [J].

HAAG, T ;

LUU, B ;

HETRU, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2353-2363

[12]

HETRU C, 1983, NOUV J CHIM, V7, P587

[13] ADULT OVARIES OF LOCUSTA-MIGRATORIA CONTAIN SEQUENCE OF BIOSYNTHETIC INTERMEDIATES FOR ECDYSONE [J].

HETRU, C ;

LAGUEUX, M ;

BANG, L ;

HOFFMAN, JA .

LIFE SCIENCES, 1978, 22 (23) :2141-2154

[14] THE BIOSYNTHETIC-PATHWAY OF ECDYSONE - STUDIES WITH VITELLOGENIC OVARIES OF LOCUSTA-MIGRATORIA (ORTHOPTERA) [J].

HETRU, CC ;

KAPPLER, C ;

HOFFMANN, JA ;

NEARN, R ;

BANG, L ;

HORN, DHS .

MOLECULAR AND CELLULAR ENDOCRINOLOGY, 1982, 26 (1-2) :51-80

[15] ZUR CHEMIE DES ECDYSONS .7. DIE KRISTALL- UND MOLEKULSTRUKTURANALYSE DES INSEKTENVERPUPPUNGSHORMONS ECDYSON MIT DER AUTOMATISIERTEN FALTMOLEKULMETHODE [J].

HUBER, R ;

HOPPE, W .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (07) :2403-&

[16] STEREOCONTROLLED CATALYTIC HYDROGENATIONS OF 3-OXOCHOLESTANES AND SOME RELATED-COMPOUNDS TO THE CORRESPONDING AXIAL 3-ALCOHOLS [J].

ISHIGE, M ;

SHIOTA, M .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (11) :1061-1068

[17] FURTHER CHARACTERIZATION OF THE 2-DEOXYECDYSONE C-2 HYDROXYLASE FROM LOCUSTA-MIGRATORIA [J].

KABBOUH, M ;

KAPPLER, C ;

HETRU, C ;

DURST, F .

INSECT BIOCHEMISTRY, 1987, 17 (08) :1155-1161

[18] STUDIES ON THE C-2 HYDROXYLATION OF 2-DEOXYECDYSONE IN LOCUSTA-MIGRATORIA [J].

KAPPLER, C ;

KABBOUH, M ;

DURST, F ;

HOFFMANN, JA .

INSECT BIOCHEMISTRY, 1986, 16 (01) :25-32

[19] CHARACTERIZATION OF 3 HYDROXYLASES INVOLVED IN THE FINAL STEPS OF BIOSYNTHESIS OF THE STEROID-HORMONE ECDYSONE IN LOCUSTA-MIGRATORIA (INSECTA, ORTHOPTERA) [J].

KAPPLER, C ;

KABBOUH, M ;

HETRU, C ;

DURST, F ;

HOFFMANN, JA .

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1988, 31 (06) :891-898

[20]

KIRK DN, 1968, MONOGRAPH, V7, P69