267011-39-2Relevant articles and documents
Total synthesis of a nonclassical bioactive acetogenin, (+)-muconin
Yang, Wen-Qian,Kitahara, Takeshi
, p. 1451 - 1461 (2000)
A convergent total synthesis of the tetrahydropyran-bearing acetogenin (+)-muconin 1 is described. All five chiral building blocks 7, 9, 17, 21, and 29 were prepared from D-glutamic acid, respectively. Four out of them were used to furnish the alkyne 16 and the iodoalkyne 33, respectively, and palladium(0)-mediated cross-coupling of alkynes 16 and 33, followed by hydrogenation, afforded 36. Simultaneous deprotection of the MOM and TBS groups in 36 with BF3·Et2O in the presence of Me2S provided (+)-muconin 1. (C) 2000 Elsevier Science Ltd.