67304-14-7Relevant academic research and scientific papers
Simple synthesis of karahanaenone
Konstantinovic, S.,Bugarcic, Z.,Marjanovic, Lj.,Gojkovic, S.,Mihailovic, M. Lj.
, p. 1169 - 1170 (2007/10/03)
Karahanaenone 1 has been prepared from linalool 3. Linalool 3 is cyclized to the corresponding tetrahydrofuran-type cyclic ethers 4a-c on treatment with PhSeCl, N-bromosuccinimide, and 3-chloroperbenzoic acid, respectively. 4a-c on further treatment with various reagents, provide allylic cyclic ether 6 which is converted to 1 via 2.
A General Approach to the Synthesis of Butanolides: Synthesis of the Sex Pheromone of the Japanese Beetle
Baskaran, Sundarababu,Islam, Imadul,Chandrasekaran, Srinivasan
, p. 891 - 895 (2007/10/02)
A variety of substituted γ-hydroxy olefins 1 have been converted to butanolides 4 in very high yield in a three-step sequence involving bromoetherification, elimination, and oxidative cleavage.The key step in the overall transformation is the highly selective oxidative cleavage of enol ethers 3 with PCC under very mild reaction conditions.Application of this methodology has been exemplified in the synthesis of the Japanese beetle pheromone.
ORGANOALUMINIUM ASSISTED REARRANGEMENTS OF FIVE-MEMBERED RING ENOL ETHERS WITH VINYL SUBSTITUENTS
Mori, Ichiro,Takai, Kazuhiko,Oshima, Koichiro,Nozaki, Hitosi
, p. 4013 - 4018 (2007/10/02)
Such organoaluminium reagents as iBu3Al, PhCCAlEt2, and Et2AlSPh mediate the title reactions in three different directions. (1) sigmatropic rearrangement producing 7-membered rings. (2) isomerization to form vinylcyclopropane derivatives and (3) SN2' type reaction with phenylthio anion via oxolane ring opening.
