Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
Conversion of Limonene to Prostanoic Acid and 8-Isoprostanoic Acid
HIROSHI SUEMUNETETSUYA KAWAHARAKIYOSHI SAKAI
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Keywords: limonene
JOURNALS FREE ACCESS

1986 Volume 34 Issue 2 Pages 550-557

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Abstract

Prostanoic acid (18) and 8-isoprostanoic acid (1) constitute the basic structures of primary prostaglandins and 8-isoprostaglandins. The conversion of commercially available (+)- and (-)-limonene to these compounds was accomplilshed by a sequence of reactions involving the Rh(I)-catalyzed cyclization of 3, 4-disubstituted 4-pentenals, which were easily prepared from (+)- or (-)-limonene, to cis-3, 4-disubstituted cyclopentanones and the appropriate modification of substituents on the five-membered ring.

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© The Pharmaceutical Society of Japan
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