Asymmetric synthesis of heteroorganic analogs of natural products. 6. (S)-?-amino-?-phosphonocarboxylic acids

Author(s):  
V. A. Soloshonok ◽  
N. Yu. Svistunova ◽  
V. P. Kukhar' ◽  
V. A. Solodenko ◽  
N. A. Kuz'mina ◽  
...  
ChemInform ◽  
2015 ◽  
Vol 46 (7) ◽  
pp. no-no
Author(s):  
Jie Yu ◽  
Ya Zhou ◽  
Dian-Feng Chen ◽  
Liu-Zhu Gong

2014 ◽  
Vol 10 ◽  
pp. 1228-1232 ◽  
Author(s):  
Jens Schmidt ◽  
Zeinab Khalil ◽  
Robert J Capon ◽  
Christian B W Stark

The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.


Marine Drugs ◽  
2018 ◽  
Vol 17 (1) ◽  
pp. 3 ◽  
Author(s):  
Takehiro Matsubara ◽  
Masashi Yokoya ◽  
Natchanun Sirimangkalakitti ◽  
Naoki Saito

A general protocol for the asymmetric synthesis of 3-N-arylmethylated right-half model compounds of renieramycins was developed, which enabled structure–activity relationship (SAR) study of several 3-N-arylmethyl derivatives. The most active compound (6a) showed significant cytotoxic activity against human prostate cancer DU145 and colorectal cancer HCT116 cell lines (IC50 = 11.9, and 12.5 nM, respectively).


2019 ◽  
Vol 21 (21) ◽  
pp. 8705-8707 ◽  
Author(s):  
Michael Schneider ◽  
Matthieu J. R. Richter ◽  
Simon Krautwald ◽  
Erick M. Carreira

1998 ◽  
Vol 35 (5) ◽  
pp. 1057-1064 ◽  
Author(s):  
Masakatsu Shibasaki ◽  
Akihiko Kojima ◽  
Satoshi Shimizu

Author(s):  
Hongbin Zhai ◽  
Yun Li ◽  
Bin Cheng ◽  
Zhiqiang Ma ◽  
Peng Gao ◽  
...  

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