13456-36-5Relevant articles and documents
Synthesis of (+)-sclareolide based on a cyclic enol ether ring contraction induced by peroxy acids
Castro, Juan M.,Salido, Sofía,Sánchez, Adolfo,Altarejos, Joaquín
, p. 2747 - 2750 (2010)
(+)-Sclareolide has been synthesised from (+)-sclareol oxide in one step in high yield, by treatment with peroxy acids under very mild conditions. The reaction pathway does not follow the usual oxidative cleavage of the double bond of (+)-sclareol oxide, but the key intermediate is a five-membered ring hemiketal. The direct conversion of a six-membered cyclic enol ether into a γ-lactone is described for the first time.
PROCESS FOR THE CYCLODEHYDRATION OF DIOLS AND USE THEREOF FOR THE MANUFACTURING OF AMBRAFURAN AND OTHER CYCLOETHER DERIVATIVES
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, (2013/03/26)
The present invention relates to a process for manufacturing tetrahydrofuran, tetrahydropyran and, more generally, cycloether derivatives through the cyclodehydration of 1,4- or 1,5- diols. More specifically, the process of the invention involves (i) the stereoselective cyclodehydration in water of 1,4- or 1,5- diols comprising at least one chiral tertiary alcohol functional group with retention of the initial chirality, and/or (ii) the cyclodehydration in water of 1,4- or 1,5- diols, said diols being non-miscible with and/or non-soluble in water, into corresponding cycloether derivatives, by bringing the reaction mixture to high temperature water (HTW) conditions and/or by mixing the aqueous reaction mixture with a solid catalyst, such as for example a smectite clay. The present invention further relates to the use of the process of the invention for manufacturing ambrafuran, especially (-)-ambrafuran and other cycloether derivatives.
