TY - JOUR
T1 - Convenient route to both enantiomerically pure forms of trans-4,5-dihydroxy-2-cyclopenten-1-one
T2 - Efficient synthesis of the neocarzinostatin chromophore core
AU - Toyama, K.
AU - Iguchi, S.
AU - Sakazaki, H.
AU - Oishi, T.
AU - Hirama, M.
PY - 2001/6
Y1 - 2001/6
N2 - An enantioselective synthesis of an epoxybicyclo[7.3.0]dodecenediyne core system of the neocarzinostatin chromophore has been achieved via intramolecular acetylide addition and palladium-mediated coupling of iodocyclopentene 5 with alkyne 6. The key cyclopentene moiety, trans-4,5-dihydroxy-2-cyclopenten-1-one 7, was conveniently prepared in both enantiomerically pure forms via enzymatic desymmetrization of meso-3,4,5-trans,trans-trihydroxycyclopentene derivatives.
AB - An enantioselective synthesis of an epoxybicyclo[7.3.0]dodecenediyne core system of the neocarzinostatin chromophore has been achieved via intramolecular acetylide addition and palladium-mediated coupling of iodocyclopentene 5 with alkyne 6. The key cyclopentene moiety, trans-4,5-dihydroxy-2-cyclopenten-1-one 7, was conveniently prepared in both enantiomerically pure forms via enzymatic desymmetrization of meso-3,4,5-trans,trans-trihydroxycyclopentene derivatives.
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U2 - 10.1246/bcsj.74.997
DO - 10.1246/bcsj.74.997
M3 - Article
AN - SCOPUS:0034928828
SN - 0009-2673
VL - 74
SP - 997
EP - 1008
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 6
ER -