17458-33-2Relevant academic research and scientific papers
Total Syntheses of (-)-Methyl Atis-16-en-19-oate, (-)-Methyl Kaur-16-en-19-oate, and (-)-Methyl Trachyloban-19-oate by a Combination of Palladium-Catalyzed Cycloalkenylation and Homoallyl-Homoallyl Radical Rearrangement
Toyota, Masahiro,Wada, Toshihiro,Ihara, Masataka
, p. 4565 - 4570 (2007/10/03)
Asymmetric total syntheses of (-)-methyl atis-16-en-19-oate (1c), (-)-methyl kaur-16-en-19-oate (2c), and (-)-methyl trachyloban-19-oate (3c) have been achieved by employing a hybrid strategy of palladium-catalyzed cycloalkenylation and homoallyl-homoallyl radical rearrangement. The common synthetic intermediate 5 was prepared from 2-allylcyclohexanone (4) with 98% ee using d'Angelo's asymmetric Michael addition. A series of functional group modifications in 5 via palladium-catalyzed cycloalkenylation led to (+)-14, which had already been prepared by us as racemate. (-)-Methyl atis-16-ene-19-oate (1c) was generated via homoallyl-homoallyl radical rearrangement. On the other hand, Wolff-Kishner reduction of 18 followed by esterification yielded (-)-methyl kaur-16-en-19-oate (2c) together with (-)-methyl trachyloban-19-oate (3c).
