488791-26-0Relevant articles and documents
Olefin Cross-Metathesis as a Tool in Natural Product Degradation. The Stereochemistry of (+)-Falcarindiol
Ratnayake, Anokha S.,Hemscheidt, Thomas
, p. 4667 - 4669 (2002)
(Matrix Presented) There are conflicting reports in the literature concerning the absolute sterochemistry at C-3 of the common plant polyacetylene oxylipin (+)-falcarindiol. We have employed olefin cross-metathesis using Grubbs' second generation catalyst and ethylene gas to degrade falcarindiol to the symmetrical 1,9-decadiene-4,6-diyne-3,8-diol. The reaction is completely selective for net removal of the aliphatic side chain. Degradation of (+)-falcarindiol from Tetraplasandra hawaiiensis yields a meso product as shown by chiral HPLC. Hence, (+)-falcarindiol from this source has a (3R,8S)-configuration.