New orthogonally functionalized synthetic blocks from R-(−)-carvone

Abstract

The intramolecular cyclization of (-)-cis-carveol under iodine treatment afforded (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene that was subjected to allyl oxydation with the complex CrO 3 DMP giving a synthetically valuable building block, (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene-4-one. In the latter the double bond was cleaved by ozonization to obtain the expected trioxo derivative, and the subsequent ozonolysis of its enol form provided a multiple functionalized tetrahydrofuran derivative.

Titanium carbenoid-mediated cyclopropanation of allylic alcohols: selectivity and mechanism

“…This compound was obtained by means of the procedure described in the literature and its spectroscopic data were identical to those described in the literature. 34 Preparation of 6a. This compound was obtained by means of the procedure described in the literature and its spectroscopic data were identical to those described in the literature.…”

Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism

“…This compound was prepared following a procedure reported in the literature. NMR data were identical to those described in the literature …”

Hydrotalcite catalysis for the synthesis of new chiral building blocks

“…it has been demonstrated that the use of hydrotalcites made possible to obtain in good yield from a commercially available material in both enantiomeric pure forms chiral compounds such as lactones 7 and 8 that can be used in organic synthesis as valuable synthons (Valeev et al 2010).…”