193071-32-8

Upstream product

• 261511-22-2 (1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol 
• 144938-82-9 (1S,4R)-(+)-4-(Hydroxymethyl)cyclopent-2-enol 
• 934986-74-0 (1R,4R)-4-(benzyloxymethyl)cyclopent-2-enol 
• 193071-31-7 (1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-yl acetate 
• 542-92-7 cyclopenta-1,3-diene 
• 60176-77-4 (1S,4R)-4-hydroxy-2-cyclopentenyl acetate 
• 29783-26-4 cis-4-cyclopentene-1,3-diol 
• 54664-61-8 cis-1,4-diacetoxy-2-cyclopentene 
• 261511-24-4 [(1S)-cis-1-(4-Benzyloxymethylcyclopent-2-en-1-yloxy)ethenyloxy] tert-butyldimethylsilane 

Downstream Products

• 261511-37-9 (1R,4R,5S)-(5-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl)acetic acid 
• 485-43-8 iridomyrmecin 
• 193141-50-3 (3aR,4R,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one 
• 261511-35-7 (2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid 
• 261511-33-5 (3S,3aS,4R,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-3-methylcyclopenta[b]furan-2-one 
• 261511-29-9 (3aR,4R,6R,6aS)-4-Benzyloxymethyl-6-iodohexahydrocyclopenta[b]furan-2-one 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure cyclopentene building blocks

An efficient synthesis of the enantiomerically pure cis-annulated cyclopentenes 2 and ent-2 was established by the use of an enzymatic transesterification and hydrolysis, respectively, followed by an S N2-type substitution with a benzyloxymethyl cuprate and a sigmatropic rearrangement. The advantage of this approach is the short sequence combined with an excellent overall yield and an enantiomeric excess of 99%. Georg Thieme Verlag Stuttgart.

Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols

The preparation and lithium amide-induced rearrangements of 1,2-dideuterated 4-substituted cyclopentene oxides 11 and 19 are described, providing insight into the deprotonation mechanisms operating in such systems. Highly enantioselective syntheses of 4-substituted cis-4-hydroxymethylcyclopent-2-en-1-ols 32a-c are described. Also described are asymmetric syntheses of prostaglandin precursor 40 and (+)-iridomyrmecin (48) via highly enantioselective rearrangement of the epoxide 3 and subsequent Ireland-Claisen rearrangement. The Royal Society of Chemistry 1999.

An Enantioselective Epoxide Rearrangement - Claisen Rearrangement Approach to Prostaglandins and (+)-Iridomyrmecin

The asymmetric syntheses of prostaglandin precursor 8 and (+)iridomyrmecin (12) via highly enantioselective rearrangement of the epoxide 1 and subsequent Ireland-Claisen rearrangement are described.