183612-91-1

Upstream product

• 98-00-0 (2-furyl)methyl alcohol 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 110366-41-1 -3-(benzyloxy)-4-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>cyclopentanone 
• 150338-77-5 (1R,4S)-cis-1-benzyloxycyclopent-2-en-4-ol 
• 183612-92-2 (1S,4R)-4-(benzyloxy)cyclopent-2-en-1-yl acetate 
• 188434-69-7 (1R,4S)-4-(benzyloxy)cyclopent-2-en-1-yl acetate 
• 150338-78-6 (1S,4R)-cis-1-benzyloxycyclopent-2-en-4-ol 

Relevant academic research and scientific papers

The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol

The preparation and enzymatic resolution of several cis-mono-4-O-protected-2-cyclopenten-1,4-diols are described. The process starts with inexpensive furfuryl alcohol and lends itself to the preparation of multigram quantities of various protected, optically active 2-cyclopenten-1,4-diol derivatives. Stereoselective reduction of 4-O-protected-2-cyclopentenone to the cis-mono-O-protected-2-cyclopenten-1,4-diol using LiAlH4/LiI or Red-Al/NaI is described. Subsequent pancreatin-promoted, stereoselective acylation was conducted on these cis-(+/-)-mono-O-protected-cyclopenten-1,4-diols to afford the corresponding alcohols and acetates in moderate to excellent enantioselectivities.