Oxidative degradation of a steroidal isoxazoline: 1-formyl-7-methoxy-2-methylphenanthrene from 3\'-methoxyestra-1\',3\',5\'(10\')-trieno(16\',17\':4,5)isoxazoline

Thies Thiemann; Shuntaro Mataka; Christian Burmester; Masataka Watanabe; Masao Imai

doi:10.3390/ecsoc-13-00172

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Oxidative degradation of a steroidal isoxazoline: 1-formyl-7-methoxy-2-methylphenanthrene from 3\'-methoxyestra-1\',3\',5\'(10\')-trieno(16\',17\':4,5)isoxazoline

Thies Thiemann

^{*

1, 2},

Shuntaro Mataka

³,

Christian Burmester

³,

Masataka Watanabe

¹,

Masao Imai

¹ Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1, Kasuga-koh-en, Kasuga-shi 816-8580, Fukuoka-ken, Japan
² Present address: Department of Chemistry, Faculty of Sciences, United Arab Emirates University, PO Box 17551, Al Ain, United Arab Emirates
³ Institute of Materials Chemistry and Engineering, Kyushu University, 6-1, Kasuga-koh-en, Kasuga-shi 816-8580, Fukuoka-ken, Japan

Published: 31 October 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-13-00172

Abstract: Estra-1,3,5(10),16-tetraene was converted to an estra-1\',3\',5\'(10\')- trieno(16\',17\':4,5)isoxazoline. The isoxazoline was transformed to a substituted 1- formylphenanthrene by the action of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ).

Keywords: Estrane, steroid, isoxazole, dehydrogenation, 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)

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Thies Thiemann

Shuntaro Mataka

Christian Burmester

Masataka Watanabe

Masao Imai