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Molecules 2017, 22(12), 2032; doi:10.3390/molecules22122032

Hydroboration-Oxidation of (±)-(1α,3α,3aβ,6aβ) -1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products

1
National Institute for Chemical-Pharmaceutical Research and Development, Department of bioactive substances and pharmaceutical technologies, 112 Vitan Av., 031299, Bucharest-3, Romania
2
Organic Chemistry Center “C.D.Nenitescu”, Spectroscopy Laboratory, 202 B Splaiul Independentei, 060023 Bucharest, Romania
3
Institute of Macromolecular Chemistry “Petru Poni”, Crystallography Department, 700478 Iasi, Romania
*
Author to whom correspondence should be addressed.
Received: 22 October 2017 / Revised: 15 November 2017 / Accepted: 16 November 2017 / Published: 24 November 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

Hydroboration-oxidation of 2α,4α-dimethanol-1β,5β-bicyclo[3.3.0]oct-6-en dibenzoate (1) gave alcohols 2 (symmetric) and 3 (unsymmetric) in ~60% yield, together with the monobenzoate diol 4a (37%), resulting from the reduction of the closer benzoate by the intermediate alkylborane. The corresponding alkene and dialdehyde gave only the triols 8 and 9 in ~1:1 ratio. By increasing the reaction time and the temperature, the isomerization of alkylboranes favours the un-symmetrical triol 9. The PDC oxidation of the alcohols gave cleanly the corresponding ketones 5 and 6 and the deprotection of the benzoate groups gave the symmetrical ketone 14, and the cyclic hemiketal 15, all in high yields. The ethylene ketals of the symmetrical ketones 11 and 13 were also obtained. The compounds 5, 6, 11, 13, 14 could be used for synthesis of new (iso)carbacyclin analogues. The structure of the compounds was established by NMR spectroscopy and confirmed by X-ray crystallography. View Full-Text
Keywords: hydroboration-oxidation; borane; sodium acetoxyborohydride; hexahydro-1,3-pentalenedimethanol; octahydropentalene-triols; octahydropentalene-ketones; X-ray analysis hydroboration-oxidation; borane; sodium acetoxyborohydride; hexahydro-1,3-pentalenedimethanol; octahydropentalene-triols; octahydropentalene-ketones; X-ray analysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tănase, C.I.; Cocu, F.G.; Căproiu, M.T.; Drăghici, C.; Shova, S. Hydroboration-Oxidation of (±)-(1α,3α,3aβ,6aβ) -1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products. Molecules 2017, 22, 2032.

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