MCPB treatment of (±)-(1α,3α,3aβ,6aβ)-1,2,3,3a,4,6a-hexahydro-1,3-pentalenedimethanol and its O-acyl-protected derivatives; X-ray crystallography

Add time:08/24/2019    Source:sciencedirect.com

The treatment of hexahydro-1.3-pentalenedimethanol 1 with MCPB acid gave a pentalenofurane compound 7 instead of an epoxide, in >90% yield by participation of the closer hydroxymethyl group in epoxidation. Acyl-protected derivatives 1a–1e gave a mixture of exo- and endo-epoxides 5/6 as expected, with exo-epoxides representing the major compound in all cases. The best yield for exo-epoxide was obtained for diacetate 1a. Basic hydrolysis of exo-epoxides gave the pentalenofurane compound 7, while that of the endo-epoxide 6c gave the unsubstituted endo-epoxide 6. The structure of the compounds was confirmed by IR, MS, 1H and 13C NMR spectra and also by extensive X-ray crystallography of compounds 7c, 7d, 5a, 6c and 7.

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