338386-45-1Relevant articles and documents
N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (-)-TAN1251A.
Wardrop,Basak
, p. 1053 - 1056 (2001)
[structure: see text]. A formal synthesis of the muscarinic M(1) receptor antagonist (-)-TAN1251A (7) from L-tyrosine is described. Central to this venture has been the construction of the 1-azaspiro[4.5]decane skeleton present in the natural product by a
Photoinduced electron transfer-promoted debenzylation of phenylalanine and tyrosine derivatives using dicyanoarene
Yamawaki, Mugen,Okita, Yoshiki,Yamamoto, Takashi,Morita, Toshio,Yoshimi, Yasuharu
, p. 7239 - 7244 (2017/11/20)
Photoinduced debenzylations of phenylalanine and tyrosine derivatives with dicyanoarenes afford glycine derivatives by the generation of radical cations. Despite the limited substrate scope, the radical cation of phenylalanine and tyrosine derivatives bearing both a carbamate (without an aromatic group) at the N-terminal and an amide at the C-terminal could promote the breaking C–C bond at the benzylic position by a photoinduced electron transfer. It is important to understand the chemical behavior of the radical cations of phenylalanine and tyrosine in enzymes involving electron transfer.
Total synthesis of tricyclic azaspirane derivatives of tyrosine: FR901483 and TAN1251C
Ousmer,Braun,Bavoux,Perrin,Ciufolini
, p. 7534 - 7538 (2007/10/03)
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.