248948-75-6Relevant academic research and scientific papers
Rapid Syntheses of (?)-FR901483 and (+)-TAN1251C Enabled by Complexity-Generating Photocatalytic Olefin Hydroaminoalkylation
Reich, Dominik,Trowbridge, Aaron,Gaunt, Matthew J.
, p. 2256 - 2261 (2020/01/24)
We report a common strategy to facilitate the syntheses of the polycyclic alkaloids (?)-FR901483 (1) and (+)-TAN1251C (2). A divergent synthetic strategy provides access to both natural products through a pivotal spirolactam intermediate (3), which can be accessed on a gram-scale. A photocatalytic olefin hydroaminoalkylation brings together three readily available building blocks and forges the majority of the carbon framework present in 1 and 2 in a single operation, leading to concise total syntheses. The complexity-generating photocatalytic process also provides direct access to novel non-racemic spirolactam scaffolds that are likely to be of interest to early-stage drug discovery programs.
Enantioselective total syntheses of (-)-FR901483 and (+)-8- epi -FR901483
Huo, Hao-Hua,Xia, Xiao-Er,Zhang, Hong-Kui,Huang, Pei-Qiang
, p. 455 - 465 (2013/02/25)
The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.
Total synthesis of (-)-FR901483
Ma, Ai-Jun,Tu, Yong-Qiang,Peng, Jin-Bao,Dou, Qing-Yun,Hou, Si-Hua,Zhang, Fu-Min,Wang, Shao-Hua
supporting information; experimental part, p. 3604 - 3607 (2012/09/11)
A total synthesis of the immunosuppressive alkaloid (-)-FR901483 (1) has been described. The intriguingly azatricyclic structure of 1 was constructed by the semipinacol-type rearrangement and intramolecular Schmidt reaction of an azido cyclohexanone deriv
Stereocontrolled total synthesis of (-)-FR901483
Ieda, Shigeru,Masuda, Akitaka,Kariyama, Mami,Wakimoto, Toshiyuki,Asakawa, Tomohiro,Fukuyama, Tohru,Kan, Toshiyuki
, p. 1071 - 1092 (2013/08/23)
The total synthesis of a potent immunosuppressant (-)-FR901483 is accomplished. The skeleton itself is constructed by the Ugi 4CC reaction, subsequent intramolecular Dieckmann condensation, and a diastereoselective intramolecular aldol reaction. However, the remarkable feature is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the tricyclic core skeleton.
Synthetic ventures inspired by biosynthetic hypotheses: the evolution of a method for the oxidative amidation of phenols
Ciufolini, Marco A.,Canesi, Sylvain,Ousmer, Malika,Braun, Norbert A.
, p. 5318 - 5337 (2007/10/03)
We describe the development of a technique for the oxidative conversion of 4-alkyl phenols to derivatives of the corresponding 4-alkyl-4-amino-2,5-cyclohexanediones. This transformation, which was inspired by biogenetic considerations, constitutes a key s
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.
Total Synthesis of (-)-FR901483
Snider, Barry B.,Lin, Hong
, p. 7778 - 7786 (2007/10/03)
The first synthesis of the immunosuppressant (-)-FR901483 (1) has been accomplished in 2% overall yield from O-methyltyrosine methyl ester (31) in 22 steps establishing the absolute stereochemistry of the natural product. A 1,3-dipolar cycloaddition of ni
