TY - JOUR
T1 - Total synthesis of madindoline A
AU - Hosokawa, Seijiro
AU - Kobayashi, Susumu
N1 - Funding Information:
We thank Prof. Satoshi Ōmura (Kitasato Institute) for providing NMR spectra of madindoline A and B. We also thank Dr Toshiaki Sunazuka (Kitasato University) for helpful discussions. This work was supported in part by the Fujisawa Foundation (S.H.) and Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan.
PY - 2001/11
Y1 - 2001/11
N2 - The total synthesis of madindolin A was achieved. Stereoselective construction of the quaternary carbon in the cyclopentenedione moiety was accomplished by alkylation of dienolate bearing a chiral auxiliary. The coupling of sterically hindered aldehyde 17 and acid-sensitive amine 30 was achieved by developing a new reductive amination method using Sn(OTf)2 and NaBH(OAc)3. After the reductive coupling, the cyclopentenedione skeleton of madindoline was constructed by intramolecular condensation of triketone 5.
AB - The total synthesis of madindolin A was achieved. Stereoselective construction of the quaternary carbon in the cyclopentenedione moiety was accomplished by alkylation of dienolate bearing a chiral auxiliary. The coupling of sterically hindered aldehyde 17 and acid-sensitive amine 30 was achieved by developing a new reductive amination method using Sn(OTf)2 and NaBH(OAc)3. After the reductive coupling, the cyclopentenedione skeleton of madindoline was constructed by intramolecular condensation of triketone 5.
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U2 - 10.5059/yukigoseikyokaishi.59.1103
DO - 10.5059/yukigoseikyokaishi.59.1103
M3 - Review article
AN - SCOPUS:0035519734
SN - 0037-9980
VL - 59
SP - 1103
EP - 1108
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
IS - 11
ER -