FUNCTIONALIZATION OF STEROID SIDE-CHAINS - CONVERSION OF CHOLESTEROL TO CHOL-5-ENE-3-BETA, 24-DIOL

被引:15
作者
DENO, NC
MEYER, MD
机构
[1] Department of Chemistry, The Pennsylvania State University, Pennsylvania 16802, University Park
关键词
D O I
10.1021/jo01333a022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cholesterol has been converted to choI-5-ene-3/3, 24-diol in a 14% overall yield. The three-step process involves protection of the double bond of cholesterol as 6/3-acetamido-5a-cholestan-3/3-ol acetate (1), elimination of the three terminal carbons of the side chain by a novel oxidative cleavage with trifluoroperoxyacetic acid, and elimination of acetamide to restore the 5, 6 double bond. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:3383 / 3385
页数:3
相关论文
共 16 条
  • [1] NITRATION OF UNSATURATED STEROIDS
    ANAGNOSTOPOULOS, CE
    FIESER, LF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (02) : 532 - 536
  • [2] BOCKOVA H, 1966, COLLECT CZECH CHEM C, V31, P3790
  • [3] CHARACTERIZATION OF STEROLS BY GAS CHROMATOGRAPHY-MASS SPECTROMETRY OF TRIMETHYLSILYL ETHERS
    BROOKS, CJW
    HORNING, EC
    YOUNG, JS
    [J]. LIPIDS, 1968, 3 (05) : 391 - &
  • [4] SYNTHESIS OF 25-HYDROXYCHOLECALCIFEROL BIOLOGICALLY EFFECTIVE METABOLITE OF VITAMIN D3
    CAMPBELL, JA
    SQUIRES, DM
    BABCOCK, JC
    [J]. STEROIDS, 1969, 13 (05) : 567 - &
  • [5] DENO NC, 1976, J CHEM SOC CHEM COMM, P1051
  • [6] HYDROXYLATION OF ALKANES AND ALKYL CHAINS
    DENO, NC
    JEDZINIAK, EJ
    MESSER, LA
    MEYER, MD
    STROUD, SG
    TOMEZSKO, ES
    [J]. TETRAHEDRON, 1977, 33 (19) : 2503 - 2508
  • [7] FROMMER U, 1971, Z NATURFORSCH PT B, VB 26, P322
  • [8] OXENOID MODELS FOR ENZYMIC HYDROXYLATIONS
    HAMILTON, GA
    GIACIN, JR
    HELLMAN, TM
    SNOOK, ME
    WELLER, JW
    [J]. ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, 1973, 212 (JUN22) : 4 - 12
  • [9] OXIDATIONS WITH PEROXYTRIFLUOROACETIC ACID-BORON FLUORIDE
    HART, H
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (10) : 337 - &
  • [10] STEROIDS .2. 6-AMINO STEROIDS
    KETCHESON, BG
    TAURINS, A
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1960, 38 (06): : 981 - 986