251998-93-3

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 251998-91-1 (R)-7-trimethylsilyl-6-heptyne-1,2-diol 
• 251998-64-8 (R)-1,2-O-isopropylidene-7-trimethylsilyl-6-heptyne-1,2-diol 
• 251998-89-7 (R)-5-iodo-1,2-O-isopropylidenepentane-1,2-diol 
• 133008-08-9 (4R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol 

Relevant academic research and scientific papers

Total synthesis of a nonclassical bioactive acetogenin, (+)-muconin

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.

Convergent synthesis of (+)-muconin

An efficient total synthesis of the tetrahydropyran-bearing acetogenin muconin 1 is described. Palladium(0)-mediated crossed diyne coupling and the use of only D-glutamic acid as the origin of all absolute stereochemistry highlight this flexible approach that sets the stage for access to structural analogs for further study.