Towards Synthesis of Calysterols, Marine Sterols with Cyclopropene Moiety in the Side Chain: Synthesis of 26,27-Dinor-23H-isocalysterol

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Title:Towards Synthesis of Calysterols, Marine Sterols with Cyclopropene Moiety in the Side Chain: Synthesis of 26,27-Dinor-23H-isocalysterol
Creators:
Kurek-Tyrlik, Alicja
Minksztym, Kazimierz
Wicha, Jerzy
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 10, pp. 1575-1588
Uncontrolled Keywords:Marine natural products, Cyclopropenes, Total synthesis, Cyclopropanes, Steroids, Steroid side chain construction

Abstract

26,27-Dinor-23<i>H</i>-isocalysterol <strong>24</strong> has been synthesized in 19% yield (6 steps) from ethyl 6β-methoxy-3α,5-cyclo-5α-pregnan-21-oate (<strong>18</strong>). For construction of the side chain, alkylation of lithium salt of ester <strong>18</strong> with 1-bromo-1,2-dimethyl-<i>c</i>-3-iodomethyl-<i>c</i>-2-(trimethylsilyl)cyclopropane <strong>16</strong> was used. It has been shown that reduction of the ester group in position 21 and rearrangement of the 3,5-cyclosteroid system are compatible with the sidechain functionalities. It has been found that methylation of 1,1-dibromo-2-(trimethylsilyl)cyclopropane is accompanied by an rearrangement involving 1,2-migration of the trimethylsilyl group.

Title:Towards Synthesis of Calysterols, Marine Sterols with Cyclopropene Moiety in the Side Chain: Synthesis of 26,27-Dinor-23H-isocalysterol
Creators:
Kurek-Tyrlik, Alicja
Minksztym, Kazimierz
Wicha, Jerzy
Uncontrolled Keywords:Marine natural products, Cyclopropenes, Total synthesis, Cyclopropanes, Steroids, Steroid side chain construction
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:10
Page Range:pp. 1575-1588
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19981575UNSPECIFIED
ID Code:1403
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Kurek-Tyrlik, Alicja; Minksztym, Kazimierz; Wicha, Jerzy (1998) Towards Synthesis of Calysterols, Marine Sterols with Cyclopropene Moiety in the Side Chain: Synthesis of 26,27-Dinor-23H-isocalysterol. Collection of Czechoslovak Chemical Communications, 63 (10). pp. 1575-1588. ISSN 0010-0765

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