Synthesis of 8,14-Secosteroids from (S)-(+)-Carvone

[img]PDF - Authorized users only
Language: English
131Kb
Title:Synthesis of 8,14-Secosteroids from (S)-(+)-Carvone
Creators:
Kotyatkina, Anna I.
Zhabinskii, Vladimir N.
Khripach, Vladimir A.
Groot, Aede de
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 7, pp. 1173-1182
Uncontrolled Keywords:Isoxazolines, Total synthesis, Terpenoids, Isoxazoles, Secosteroids, Steroids, Nitrile oxides, Carvone

Abstract

A total synthesis of functionalised 8,14-seco steroids with five- and six-membered D rings is described. The synthesis is based on the transformation of (<i>S</i>)-carvone into a steroidal AB ring moiety with a side chain at C-9 that allowed the creation of a nitrile oxide at this position. The nitrile oxides were coupled with cyclic enones or enol derivatives of 1,3-diketones, and reductive cleavage of the obtained cycloadducts gave the desired products. The formation of a twelve-membered ring compound was observed in cycloaddition of one of the nitrile oxides with cyclopentenone as the result of an intramolecular ene-reaction followed by retroaldol reaction. <p>

Title:Synthesis of 8,14-Secosteroids from (S)-(+)-Carvone
Creators:
Kotyatkina, Anna I.
Zhabinskii, Vladimir N.
Khripach, Vladimir A.
Groot, Aede de
Uncontrolled Keywords:Isoxazolines, Total synthesis, Terpenoids, Isoxazoles, Secosteroids, Steroids, Nitrile oxides, Carvone
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:65
Number:7
Page Range:pp. 1173-1182
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001173UNSPECIFIED
ID Code:1709
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:12

Citation

Kotyatkina, Anna I.; Zhabinskii, Vladimir N.; Khripach, Vladimir A.; Groot, Aede de (2000) Synthesis of 8,14-Secosteroids from (S)-(+)-Carvone. Collection of Czechoslovak Chemical Communications, 65 (7). pp. 1173-1182. ISSN 0010-0765

Repository Staff Only: item control page