123749-43-9Relevant academic research and scientific papers
The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol
Curran, Timothy T.,Hay, David A.,Koegel, Christopher P.,Evans, Jonathan C.
, p. 1983 - 2004 (1997)
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.
A new chiral route to optically pure 3-oxodicyclopentadiene: A versatile chiral cyclopentadienone synthon, via contra-steric Diels-Alder reaction
Sugahara, Tsutomu,Kuroyanagi, Yukari,Ogasawara, Kunio
, p. 1101 - 1108 (2007/10/03)
Optically pure oxodicyclopentadiene (KDP) has been prepared in both enantiomeric forms from racemic 4-tert-butoxycyclopent-2-en-1-one in three ways starting from 4-tert-butoxycyclopent-2-en-1-one involving contra-steric Diels-Alder reaction and lipase-mediated enantiospecific kinetic transesterification as key steps.
AN EFFICIENT SYNTHESIS OF cis-OXABICYCLOOCT-6-EN-3-ONE
Takano, Seiichi,Kasahara, Chiyoshi,Ogasawara, Kunio
, p. 605 - 608 (2007/10/02)
An efficient synthesis of a prostaglandin synthon (+/-)-cis-oxabicyclooct-6-en-3-one (1) has been developed using cyclopentadiene (2) as starting material.Employing the same methodology optically active (1) is also synthesized in low optical purity.
