201207-50-3Relevant articles and documents
Total synthesis of (-)-macrocarpal C. Stereoselective coupling reaction with a novel hexasubstituted benzene Cr(CO)3 complex as a biomimetic chiral benzyl cation equivalent
Tanaka, Tetsuaki,Mikamiyama, Hidenori,Maeda, Kimiya,Iwata, Chuzo,In, Yasuko,Ishida, Toshimasa
, p. 9782 - 9793 (2007/10/03)
The first total synthesis of (-)-macrocarpal C (3) is described. The synthesis features a highly stereoselective coupling reaction of silyldienol ether 6 with biomimetic benzyl cation species (R)- and (S)-B, which were generated from novel hexasubstituted benzene chromium tricarbonyl complexes (R)- and (S)-17. At the final step of the total synthesis, we developed the tris-O-demethylation of macrocarpal C trimethyl ether 34 under basic conditions using lithium p-thiocresolate. Moreover, spectroscopic evidence shows that the synthetic (-)-3 is identical to natural macrocarpal G (4).