227186-02-9

Upstream product

• 143-15-7 1-dodecylbromide 
• 227186-03-0 (2R,5R,1'S)-5-<(tert-butyldiphenylsilyloxy)methyl>-2-(1'-hydroxytridecyl)tetrahydrofuran 

Downstream Products

• 227186-04-1 (1'R,2R,5R)-5-<(tert-butyldiphenylsilyloxy)methyl>-2-<(1'-methoxymethoxy)tridecyl>tetrahydrofuran 
• 227186-07-4 (2R,5R,13'R, 1''R)-2-(1'-tert-butyldiphenylsilyloxy-13'-methoxymethoxytridecyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran 
• 227186-06-3 13-(tert-Butyl-diphenyl-silanyloxy)-1-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecan-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.

Synthesis of solamin

Total synthesis of an annonaceous acetogenin, solamin (1) is described. Direct coupling between γ-lactone (13) and mono-THF unit (12) prepared from D-glutamic acid in 16 steps gave the product (14) in excellent yield, which was converted to the title comp