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.
|ジャーナル||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|出版ステータス||Published - 2001 11月|
ASJC Scopus subject areas