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Studies in terpenoids. Part LXXI. Synthesis of $(\pm )$ -sydonic acid.

Murali, D and Rao, Krishna GS (1987) Studies in terpenoids. Part LXXI. Synthesis of $(\pm )$ -sydonic acid. In: Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 26B (2). pp. 156-157.

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Abstract

Sydonic acid $[I; R = C(OH)Me CH_2CH_2CH_2CHMe_2, R_1 = R_3 = H, R_2 = CO_2H]$ was prepd. in 2 steps via regioselective oxidn. of $I (R = R_3 = Ac, R_1 = H, R_2 = Me)$ with $Et_3(PhCH_2)N+MnO_4$ followed by treatment with $Me2CHCH_2CH_2CH_2MgBr$. Similar oxidn. of $I (R = R_3 = Ac, R_1 = R_2 = Me)$ gave 3 products, of which $I (R = R_3 = Ac, R_1 = Me, R_2 = CO_2H)$ is a precursor of pyrenochaetic acid A $(I; R = COCH:CHMe; R_1 = R_3 = Me, R_2 = CO_2H)$.

Item Type: Journal Article
Additional Information: Copyright belongs to NISCAIR
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Mar 2008
Last Modified: 27 Aug 2008 13:12
URI: http://eprints.iisc.ernet.in/id/eprint/13135

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