Synthesis of 2,24-Diepicastasterone and 3,24-Diepicastasterone as Potential Brassinosteroid Metabolites of the Cockroach Periplaneta americana

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Title:Synthesis of 2,24-Diepicastasterone and 3,24-Diepicastasterone as Potential Brassinosteroid Metabolites of the Cockroach Periplaneta americana
Creators:
Voigt, Brunhilde
Porzel, Andrea
Adam, Günter
Golsch, Dieter
Adam, Waldemar
Wagner, Christoph
Merzweiler, Kurt
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 1, pp. 91-102
Uncontrolled Keywords:Ecdysteroids, Oxidations, Steroids, Metabolism, Phytohormones, <i>Periplaneta americana</i>, Brassinosteroids, 2,24-Diepicastasterone, 3,24-Diepicastasterone

Abstract

Investigations of the metabolic conversion of the phytohormone 24-epicastasterone (<strong>1</strong>) in the cockroach <i>Periplaneta americana</i> (L.) required the synthesis of 2,24-diepicastasterone (<strong>4</strong>), 3,24-diepicastasterone (<strong>7b</strong>) and 2-dehydro-3,24-diepicastasterone (<strong>9</strong>) as reference standards. 2,24-Diepicastasterone (<strong>4</strong>) was synthesized from 2α,3α-epoxy derivative <strong>2</strong> as well as from the 2β,3β-epoxy-22,23-diol <strong>3</strong> by acid-catalyzed water addition to the epoxy function leading to the desired 2β,3α-<i>trans</i> functionality. 3,24-Diepicastasterone (<strong>7b</strong>) was prepared by NaBH<sub>4</sub>-reduction of the 3-oxo derivative <strong>6</strong>. Upon deprotection conditions from the ketol acetonides <strong>6</strong> and <strong>8</strong> in both cases 2-dehydro-3,24-diepicastasterone (<strong>9</strong>) was obtained. The structure of 2,24-diepicastasterone (<strong>4</strong>) was confirmed by X-ray analysis. <p>

Title:Synthesis of 2,24-Diepicastasterone and 3,24-Diepicastasterone as Potential Brassinosteroid Metabolites of the Cockroach Periplaneta americana
Creators:
Voigt, Brunhilde
Porzel, Andrea
Adam, Günter
Golsch, Dieter
Adam, Waldemar
Wagner, Christoph
Merzweiler, Kurt
Uncontrolled Keywords:Ecdysteroids, Oxidations, Steroids, Metabolism, Phytohormones, <i>Periplaneta americana</i>, Brassinosteroids, 2,24-Diepicastasterone, 3,24-Diepicastasterone
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:67
Number:1
Page Range:pp. 91-102
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020091UNSPECIFIED
ID Code:1908
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Voigt, Brunhilde; Porzel, Andrea; Adam, Günter; Golsch, Dieter; Adam, Waldemar; Wagner, Christoph; Merzweiler, Kurt (2002) Synthesis of 2,24-Diepicastasterone and 3,24-Diepicastasterone as Potential Brassinosteroid Metabolites of the Cockroach Periplaneta americana. Collection of Czechoslovak Chemical Communications, 67 (1). pp. 91-102. ISSN 0010-0765

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