244126-22-5Relevant academic research and scientific papers
Enantioselective Synthesis of (+)-Mitomycin K by a Palladium-Catalyzed Oxidative Tandem Cyclization
Gu, Qiang-Shuai,Yang, Dan
supporting information, p. 5886 - 5889 (2017/05/12)
The mitomycins, a family of bioactive natural products, feature a compact 6/5/5-fused polycyclic ring structure densely decorated with highly reactive and/or fragile quinone, amino ketal, and aziridine as well as carbamate moieties. It is this striking feature that has defeated numerous synthetic attempts towards these apparently small molecules, rendering them one of the most formidable targets for total synthesis. We herein report the first enantioselective synthesis of (+)-mitomycin K, a representative of G series mitomycins. The key step of this synthesis is an enantioselective oxidative cyclization catalyzed by a palladium/(+)-sparteine system that had previously been developed by our group. The robustness of this method bodes well for further applications in the asymmetric total synthesis of natural products, particularly those with characteristic 6/5/5-fused pyrroloindole skeletons.
A synthesis of the pseudopterosin A-F aglycone
Cooksey, John P.,Kocienski, Philip J.,Schmidt, Arndt W.,Snaddon, Thomas N.,Kilner, Colin A.
supporting information, p. 2779 - 2785,7 (2020/07/31)
The synthesis of the pseudopterosin A-F aglycone from 3-methylcatechol features (a) the use of asymmetric Ireland-Claisen and aryl Claisen rearrangements to install three of the four stereocentres present in the molecule and (b) an A→AB→ABC annulation strategy using ring-closing metathesis and cationic cyclisation reactions as the key steps.
Intermediate and process of preparation of ecteinascidin using such intermediate
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Page/Page column 17-18, (2008/06/13)
The present invention concerns an intermediate of the following formula I in which R1 and R2 represent independently of each other a C1-C12 alkyl group, a (C1-C12 alkoxy)carbonyl group, opt
Total synthesis of cribrostatin IV: Fine-tuning the character of an amide bond by remote control
Chan, Collin,Heid, Richard,Zheng, Shengping,Guo, Jinsong,Zhou, Bishan,Furuuchi, Takeshi,Danishefsky, Samuel J.
, p. 4596 - 4598 (2007/10/03)
We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a "lynchpin" Mannich cyclization to establish the pentacyc
Synthetic studies toward ecteinascidin 743
Chen, Xiaochuan,Chen, Jinchun,De Paolis, Michael,Zhu, Jieping
, p. 4397 - 4408 (2007/10/03)
An efficient synthesis of a fully functionalized tetracycle (A-B-C-H) 7 containing a 1,4-bridged 10-membered lactone was developed. Phenolic aldol condensation between 2-methylsesamol (15) and Garner's aldehyde provided the protected amino diol 16, which
A short enantioselective synthesis of protected L-3-hydroxy-4-methoxy-5- methyl phenylalanine and its corresponding aldehyde - A common subunit of ecteinascidin-743, safracin and congeners
De Paolis, Micha?l,Chen, Xiaochuan,Zhu, Jieping
, p. 729 - 731 (2007/10/03)
An asymmetric synthesis of appropriately protected L-3-hydroxy-4-methoxy-5- methyl phenylalanine from 3-methyl-catechol is described featuring a key enantioselective alkylation step.
Total synthesis of ecteinascidin 743
Endo, Atsushi,Yanagisawa, Arata,Abe, Masanao,Tohma, Shigemitsu,Kan, Toshiyuki,Fukuyama, Tohru
, p. 6552 - 6554 (2007/10/03)
The total synthesis of ecteinascidin 743 (1), an extremely potent antitumor agent, has been accomplished. The synthesis features Ugi's 4CC reaction, intramolecular Heck reaction, phenol-aldehyde cyclization, and acid-induced intramolecular sulfide formation. Copyright
Synthetic study on ecteinascidin 743 starting from D-glucose
Endo, Atsushi,Kann, Toshiyuki,Fukuyama, Tohru
, p. 1103 - 1105 (2007/10/03)
During the course of synthetic study on ecteinascidin 743 (1), key intermediate 5 was prepared. Stereocontrolled synthesis of 5 from D-glucose was accomplished using incorporation of two nitrogen atoms and stereoselective addition of a phenol to an imine
