Total synthesis of tricyclic azaspirane derivatives of tyrosine: FR901483 and TAN1251C.
A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.
Ousmer
M
M
Laboratoire de Synthèse et Méthodologie Organiques (LSMO), UMR CNRS 5078, Université Claude Bernard Lyon 1 and Ecole Supérieure de Chimie, Physique, Electronique de Lyon, 43, Boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France.
Braun
N A
NA
Bavoux
C
C
Perrin
M
M
Ciufolini
M A
MA
D001372:Aza Compounds / Q000138:chemical synthesis; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis
D001372:Aza Compounds; C098358:FR 901483; D007166:Immunosuppressive Agents; D009943:Organophosphorus Compounds; D013141:Spiro Compounds; C429313:TAN1251A