CONVENIENT SYNTHESES OF 5,5,9-TRIMETHYL-TRANS-1-DECALONE AND 6-BETA-HYDROXY-5,5,9-BETA-TRIMETHYL-TRANS-1-DECALONE

被引：37

作者：

SNITMAN, DL

TSAI, MY

WATT, DS

EDWARDS, CL

STOTTER, PL

机构：

[1] UNIV COLORADO,DEPT CHEM,BOULDER,CO 80309

[2] UNIV TEXAS,DIV EARTH & PHYS SCI,SAN ANTONIO,TX 78285

[3] UNIV TEXAS,DEPT CHEM,AUSTIN,TX 78712

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 16期

关键词：

D O I：

10.1021/jo01330a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Convenient syntheses of 5, 5, 9-trimethyl-trarcs-1-decalone (1) and 6β-hydroxy-5, 5, 9β-trimethyl-frans-1-decalone (2) involve (1) the Robinson annelation of 2-methyl-1, 3-cyclohexanedione with ethyl vinyl ketone, (2) selective ketalization of 5, 9-dimethyl-Δ5, 10-octal-1, 6-dione at the nonconjugated carbonyl group with ethylene glycol, (3) reductive methylation of 1-ethylenedioxy-5, 9-dimethyl-Δ5, 10-2-octalone, (4) Wolff-Kishner reduction or dissolving-metal reduction of 1-ethylenedioxy-5, 5, 9-trimethyl-trans-1-decalone, and (5) acid-catalyzed hydrolysis of 1-ethylenedioxy-5, 5, 9-trimethyl-trans, 9β-trimethyl-trans-decalin to form 1 and 2, respectively. © 1979, American Chemical Society. All rights reserved.

引用

页码：2838 / 2842

页数：5

共 19 条

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