53171-64-5Relevant academic research and scientific papers
Photoinduced Vinylcyclopropane-Cyclopentene Rearrangement: A Methodology for Chiral Bicycloheptenes. Formal Syntheses of (+/-)-Grandisol and Naturally Occurring (-)-Δ9(12)-Capnellene and its Antipode
Sonawane, Harikisan R.,Naik, Vishwaniyant G.,Bellur, Nanjundiah S.,Shah, Virendra G.,Purohit, Pramod C.,et al.
, p. 8259 - 8276 (1991)
The problem of achieving reaction selectivity in cis-alkyl vinylcyclopropanes in favour of their rearrangement to cyclopentenes, obviating the competing low energy process of the (homo)sigmatropic hydrogen shift, is addressed.It has been demonstrated that the readily available bicycloheptenes derived from (+)-Δ3-carene (1), upon photosensitized irradiation, are conveniently transformed into chiral cis-bicyclo heptenes.The synthetic potential of this strategy has been demonstrated in realization of efficient formal syntheses of the important insect sex pheromone (+/-)-grandisol (2) and both the enantiomers of Δ9(12)-capnellene (3) from readily available 1, a major component of Indian turpentine oil.
SYNTHESIS OF (+/-)-GRANDISOL FROM (+) Δ2-CARENE: AN APPLICATION OF PHOTO-INDUCED VINYLCYCLOPROPANE REARRANGEMENT
Sonawane, H. R.,Nanjundiah, B. S.,Kumar, M. Udaya
, p. 2245 - 2246 (2007/10/02)
A new synthesis of (+/-)-Grandisol from (+) Δ2-carene involving the photoinduced vinylcyclopropane rearrangement (VCR) as the key step is described.
