Short total synthesis of (+)-madindolines A and B.
[reaction: see text] A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.
Hirose
Tomoyasu
T
The Kitasato Institute and School of Pharmaceutical Sciences, Kitasato University, and CREST, The Japan Science and Technology Corporation (JST), Minato-ku, Tokyo 108-8642, Japan.
Sunazuka
Toshiaki
T
Shirahata
Tatsuya
T
Yamamoto
Daisuke
D
Harigaya
Yoshihiro
Y
Kuwajima
Isao
I
Omura
Satoshi
S
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003500:Cyclization; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D013237:Stereoisomerism; D000093242:Interleukin-6 Inhibitors
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D007211:Indoles; D000093242:Interleukin-6 Inhibitors; C103158:madindoline A