Synthetic studies in quest of Platonic hydrocarbon dodecahedrane

Mehta, Goverdhan ; Raja Reddy, K. ; Nair, Mangalam S. (1988) Synthetic studies in quest of Platonic hydrocarbon dodecahedrane Proceedings of the Indian Academy of Sciences - Chemical Sciences, 100 (2-3). pp. 223-234. ISSN 0253-4134

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In pursuit of Platonic hydrocarbon dodecahedrane1, a retrosynthetic theme indicated in scheme 1, was formulated. The precursor tetraquinanedione synthon5 was first designed through a photo-thermal olefin metathesis approach. The tetraquinanedione 5 was further elaborated toexo, exo-tetraquinane diester15 through carbonyl homologation, oxidation, esterification sequence, scheme 5. Bis-cyclopentannulation ofexo,exo-diester15 by Greene methodology delivered a functionalised C20-hexaquinane44, havingexo-annulated cyclopentane rings. Cyclopentane inversion was achieved by a set of reactions involving enone generation, double bond isomerisation and hydrogenation to give spheroidal (C2v)-C20-hexaquinanedione-diester47, the penultimate precursor of dodecahedrane 1. Several interesting transformations and rearrangements of polyquinanes are also described.

Item Type:Article
Source:Copyright of this article belongs to Indian Academy of Sciences.
Keywords:Dodecahedrane; C2v-tetraquinane Dione; Cis-hexaquinane; Bis-cyclopentannulation; Cyclopentanone Inversion
ID Code:29094
Deposited On:18 Dec 2010 05:37
Last Modified:17 May 2016 12:04

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