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Total Synthesis of a Nonclassical Bioactive Acetogenin, (+)-Muconin

✍ Scribed by Wen-Qian Yang; Takeshi Kitahara

Book ID: 104202510
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 198 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00033-8

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✦ Synopsis

A convergent total synthesis of the tetrahydropyran-bearing acetogenin (ϩ)-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 BF 3 •Et 2 O in the presence of Me 2 S provided (ϩ)-muconin 1.

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