282550-29-2Relevant academic research and scientific papers
One Substrate - Seven products with different prenylation positions in one-step reactions: Prenyltransferases make it possible
Fan, Aili,Li, Shu-Ming
, p. 2659 - 2666 (2013)
Prenylated indole alkaloids derived from L-tryptophan are widely distributed in nature and show diverse biological and pharmacological activities, usually distinct from their non-prenylated precursors. Prenyltransferases catalyze the transfer reactions of
Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction
Ma,Liu,Li,Flippen-Anderson,Yu,Cook
, p. 4525 - 4542 (2007/10/03)
A novel and concise synthesis of optically active tryptophan derivatives was developed via a palladium-catalyzed heteroannulation reaction of substituted o-iodoanilines with an internal alkyne. The required internal alkyne 14a or 25 was prepared in greater than 96% de via alkylation of the Schoellkopf chiral auxiliary 19 employing diphenyl phosphate as the leaving group. The Schoellkopf chiral auxiliary was chosen here for the preparation of L-tryptophans would be available from D-valine while the D-isomers required for natural product total synthesis would originate from the inexpensive L-valine (300-g scale). Applications of the palladium-catalyzed heteroannulation reaction were extended to the first asymmetric synthesis of L-isotryptophan 38 and L-benz[f]tryptophan 39. More importantly, the optically pure 6-methoxy-D-tryptophan 62 was prepared by this protocol on a large scale (>300 g). This should permit entry into many ring-A oxygenated indole alkaloids when coupled with the asymmetric Pictet-Spengler reaction. In addition, an improved total synthesis of tryprostatin A (9a) was accomplished in 43% overall yield employing this palladium-mediated process.
Efficient asymmetric synthesis of important tryptophan analogs for biological research via the Schollkopf chiral auxiliary
Ma, Chunrong,Yu, Shu,He, Xiaohui,Liu, Xiaoxiang,Cook, James M.
, p. 2781 - 2785 (2007/10/03)
An efficient method has been developed via the Schollkopf chiral auxiliary for the asymmetric synthesis of the important tryptophan analogs: L-isotryptophan, L-benzo[f]tryptophan and L-homotryptophan. (C) 2000 Elsevier Science Ltd.
