USE OF N-LITHIOETHYLENEDIAMINE IN THE DOUBLE-BOND ISOMERIZATION AND DEGRADATION OF STEROL SIDE-CHAINS

被引：9

作者：

AYANOGLU, E ^{[1
]}

CHAN, A ^{[1
]}

DJERASSI, C ^{[1
]}

机构：

[1] STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305

来源：

TETRAHEDRON | 1979年 / 35卷 / 13期

关键词：

D O I：

10.1016/0040-4020(79)80020-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Double bond isomerization of stigmasterol ((24S)-24-ethylcholesta-5,22-dien-3β-ol) with N-lithioethy-lenediamine produced stigmasta-5,17(20)-dien-3β-ol, stigmasta-5,20(22)-dien-3β-ol, stigmasta-5,23-dien-3β-ol and stigmasta-5,24-dien-3β-ol. Some starting material was also present in the isomerization mixture along with a small amount of stigmast-5-en-3β-ol. Similar treatment of 3α,5-cyclo-6β-methoxystigmast-22-en (stigmasterol i-methyl ether) followed by ozonization and removal of the ring A-protecting group yielded predominantly 3β-hydroxy-androst-5-en-17-one and 3β-hydroxypregn-5-en-20-one. The isomerization products of fucosterol (24-ethylcholesta- 5, 24(28)E-dien-3β-ol) and 23,24-bisnorchola-5,20-dien-3β-ol are also reported. © 1979.

引用

页码：1591 / 1594

页数：4

共 17 条

[1]

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[2]

BORTOLOTTO M, 1978, B SOC CHIM BELG, V87, P539

[3]

BROWN CA, 1975, CHEM COMMUN, P222

[4] MARINE STEROLS WITH A NEW PATTERN OF SIDE-CHAIN ALKYLATION FROM SPONGE APLYSINA-(=VERONGIA)-AEROPHOBA [J].