MOULTING HORMONES OF INSECTS AND CRUSTACEANS - SYNTHESIS OF 22-DEOXYCRUSTECDYSONE

被引:21
作者
GALBRAIT.MN
HORN, DHS
MIDDLETO.EJ
HACKNEY, RJ
机构
[1] Division of Applied Chemistry, CSIRO Chemical Research Laboratories, Melbourne, VIC, 3001
[2] Research and Development Laboratory, Union Carbide Australia Ltd, Rhodes, NSW
关键词
D O I
10.1071/CH9691517
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A partial synthesis of the title compound (III) has been accomplished from crustecdysone (I). Chromic acid oxidation of crustecdysone afforded the ketone (VI) which was converted into the corresponding acetonide silyl ether (IX). Alkylation of (IX) with the Grignard reagent from (XI) and hydrolysis of the protecting groups afforded the required compound (III). An alternative route which facilitates tritium labelling afforded the same product. The biological activity and spectral properties of the product are discussed. © 1969, CSIRO. All rights reserved.
引用
收藏
页码:1517 / &
相关论文
共 22 条
[1]   MANY-MEMBERED CARBON RINGS .15. SYNTHESIS AND ACYLOIN CYCLIZATION OF DELTA,DELTA-DIPHENYLAZELAIC ESTER [J].
BLOMQUIST, AT ;
BUCK, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (03) :672-676
[2]   STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS [J].
CRAM, DJ ;
ELHAFEZ, FAA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) :5828-5835
[3]   INSECT MOULTING HORMONES - CRUSTECDYSONE (20-HYDROXYECDYSONE) FROM PODOCARPUS ELATUS [J].
GALBRAITH, MN ;
HORN, DHS .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (05) :1045-+
[4]   A SILYL ETHER AS A PROTECTING GROUP IN SYNTHESIS OF AN ISOMER OF ECDYSONE 20R-HYDROXY-22-DEOXYECDYSONE [J].
GALBRAITH, MN ;
HORN, DHS ;
MIDDLETO.EJ ;
HACKNEY, RJ .
CHEMICAL COMMUNICATIONS, 1968, (08) :466-+
[5]  
GALBRAITH MN, UNPUBLISHED DATA
[6]   STRUCTURE OF CRUSTECDYSONE A CRUSTACEAN MOULTING HORMONE [J].
HAMPSHIRE, F ;
HORN, DHS .
CHEMICAL COMMUNICATIONS, 1966, (02) :37-+
[7]   RESEARCHES ON ACETYLENIC COMPOUNDS .21. REFORMATSKY REACTIONS WITH PROPARGYL BROMIDES [J].
HENBEST, HB ;
JONES, ERH ;
WALLS, IMS .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (OCT) :2696-2700
[8]  
HENRY H, 1906, CR HEBD SEANC ACAD S, V143, P1221
[9]   SYNTHETIC STEROIDS WITH MOULTING HORMONE ACTIVITY [J].
HOCKS, P ;
JAGER, A ;
KERB, U ;
WIECHERT, R ;
FURLENME.A ;
FURST, A ;
LANGEMAN.A ;
WALDVOGE.G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (07) :673-&
[10]   ISOLATION OF CRUSTECDYSONE (20R-HYDROXYECDYSONE) FROM A CRAYFISH (JASUS LALANDEI H MILNE-EDWARDS) [J].
HORN, DHS ;
FABBRI, S ;
HAMPSHIRE, F ;
LOWE, ME .
BIOCHEMICAL JOURNAL, 1968, 109 (03) :399-+