Natural acetylenes. Part XL. Syntheses of polyacetylenic C18 and C16 esters with 9-ene-12,14-diyne unsaturation, and their labelling
Abstract
The esters R[CC]2·CH2CH[graphics omitted]CH·[CH2]7·CO2Me{R = Me[CH2]2, MeC
C, cis- or trans-MeCH
CH, trans-HO·CH2·CH
CH, HO·CH2·C
C, cis- or trans-MeO2C·CH
CH, MeO2C·C
C, (EtO)2CH, OHC, or, H2N·OC} were prepared from the Wittig salt Me3Si·C
C·CH2·CH2·PPh3I–via IC
C·CH2·CH[graphics omitted]CH·[CH2]7·CO2Me; several were specifically labelled [at C(9), C(17), and C(18)]. The Wittig salt offers a general route to 1-ene-4,6-diyne and more highly unsaturated skipped en-yne systems.