Synthesis of (-)-agelastatin A by [3.3] sigmatropic rearrangement of allyl cyanate.
Total synthesis of (-)-agelastatin A has been achieved starting from l-arabitol. The highlights in our synthesis include the preparation of vicinal diamine moiety by [3.3] sigmatropic rearrangement of allyl cyanate and construction of central ring-C with ring-closing metathesis.
Ichikawa
Yoshiyasu
Y
Faculty of Science, Kochi University, Kochi 780-8520, Japan. ichikawa@kochi-u.ac.jp
Yamaoka
Tomonori
T
Nakano
Keiji
K
Kotsuki
Hiyoshizo
H
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003485:Cyanates / Q000737:chemistry*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry*
D000470:Alkaloids; D000498:Allyl Compounds; D003485:Cyanates; D023303:Oxazolidinones; D013402:Sugar Alcohols; C464968:agelastatin A; C014999:arabitol