201207-54-7Relevant 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).
Macrocarpals: HIV-RTase inhibitors of Eucalyptus globulus
Nishizawa, Mugio,Emura, Makoto,Kan, Yukiko,Yamada, Hidetoshi,Ogawa, Koji,Hamanaka, Nobuyuki
, p. 2983 - 2986 (2007/10/02)
Five HIV-RTase inhibitors, macrocarpals A-E, have been isolated from Eucalyptus globulus. X-ray diffraction studies as well as spectral and chemical investigations established the structures 1,2,3,12, and 13, respectively.