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2005
Terpenes
U 0200
36- 188
PtCl2-Mediated Cycloisomerization of Unsaturated Propargylic Carboxylates.
— The PtCl2-catalyzed cycloisomerization of unsaturated propargylic carboxylates (I)
affords differently functionalized bicycloheptanol esters (II) in moderate to good yields
in a very diastereoselective manner. The cycloisomerization of trisubstituted alkenes
(VI) and (VIII) proceeds stereospecifically giving cis- or trans-products, resp., depending on the stereochemistry at the double bond of the precursor. In some cases, small
amounts of allenic by-products [cf. (III)] are formed. Basic methanolysis (K2CO3,
MeOH) of the bicyclic target compounds gives mixtures of cis and trans-caran-2-ones.
— (ANJUM, S.; MARCO-CONTELLES*, J.; Tetrahedron 61 (2005) 20, 4793-4803;
Lab. Radicales Libres, Inst. Quim. Org., E-28006 Madrid, Spain; Eng.) — Bartels
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