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Une voie d'acces a la trimethyl-4,4,7a tetrahydro-3aα,4,7,7aα (3H)-benzofurannone-2 a partir des alcoxy-5 trimethyl-4,4,7a hexahydro-3aα,4,5,6,7,7aα (3H)-benzofurannones-2
Rouessac, Annick,Rouessac, Francis,Zamarlik, Henri
, p. 199 - 203 (2007/10/02)
The 5-hydroxy 4,4,7a-trimethyl 3aα, 4,5,6,7,7aα-hexahydro (3H)-benzofuran-2-ones are obtained by cleavage of the corresponding methyl or ethyl ethers with iodotrimethylsilane.The two hydroxylactones 5 and 6 are transformed into sulfonic esters as a step towards the dehydrated lactone 7, without squeletal rearrangement.Solvolysis of the tosylate and the mesylate of 5, a cis-fused ring lactone, proceeds by completely different ways under analogous experimental procedures.Results are explained and compared to the solvolysis of some triterpenes.Experimental procedures for ether cleavage are discussed and the intermediates or by-products of these reactions are identified.
