TY - JOUR
T1 - Ring-opening cyclization of spirocyclopropanes using sulfoxonium ylides
AU - Onuki, Yuta
AU - Nambu, Hisanori
AU - Yakura, Takayuki
N1 - Publisher Copyright:
© 2020 The Pharmaceutical Society of Japan
PY - 2020
Y1 - 2020
N2 - Ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes using dimethylsulfoxonium methylide proceeded regioselectively to produce 2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-ones in good to high yields. The reactions of cycloheptane- and cyclopentane-1,3-dione-2-spirocyclopropanes could construct [7.6]- and [5.6]-fused ring systems. This reaction was also carried out using sulfoxonium ethylide, butylide, and benzylide, resulting in the formation of the corresponding 2,3-trans-disubstituted products in good to high yields, and it was shown that the dimethyl group can act as a dummy substituent. It was found that the 2- and 3-phenyhexahydrobenzopyran-5-ones can be readily converted into 5-hydroxyflavan and 5-hydroxy-isoflavan, respectively.
AB - Ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes using dimethylsulfoxonium methylide proceeded regioselectively to produce 2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-ones in good to high yields. The reactions of cycloheptane- and cyclopentane-1,3-dione-2-spirocyclopropanes could construct [7.6]- and [5.6]-fused ring systems. This reaction was also carried out using sulfoxonium ethylide, butylide, and benzylide, resulting in the formation of the corresponding 2,3-trans-disubstituted products in good to high yields, and it was shown that the dimethyl group can act as a dummy substituent. It was found that the 2- and 3-phenyhexahydrobenzopyran-5-ones can be readily converted into 5-hydroxyflavan and 5-hydroxy-isoflavan, respectively.
KW - Flavan
KW - Isoflavan
KW - Ring-opening cyclization
KW - Spirocyclopropane
KW - Sulfoxonium ylide
UR - http://www.scopus.com/inward/record.url?scp=85084328445&partnerID=8YFLogxK
U2 - 10.1248/CPB.C20-00132
DO - 10.1248/CPB.C20-00132
M3 - 学術論文
C2 - 32378546
AN - SCOPUS:85084328445
SN - 0009-2363
VL - 68
SP - 479
EP - 486
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 5
ER -