ChemInform Abstract: Total Synthesis of Sarcophytonolide H and Isosarcophytonolide D: Structural Revision of Isosarcophytonolide D and Structure-Antifouling Activity Relationship of Sarcophytonolide H.

ChemInform ◽  
2016 ◽  
Vol 47 (38) ◽  
Author(s):  
Hiroyoshi Takamura ◽  
Takahiro Kikuchi ◽  
Noriyuki Endo ◽  
Yuji Fukuda ◽  
Isao Kadota
2013 ◽  
Vol 78 (6) ◽  
pp. 2443-2454 ◽  
Author(s):  
Hiroyoshi Takamura ◽  
Hiroko Wada ◽  
Nan Lu ◽  
Osamu Ohno ◽  
Kiyotake Suenaga ◽  
...  

Author(s):  
Zhonghao Sun ◽  
Shuxian Yang ◽  
Chengfang Xu ◽  
Guoxu Ma ◽  
Li Cao ◽  
...  

(-)-Zeylenone is a promising cytotoxic agent,which is a natural product isolated from Uvaria grandiflora Roxb. Though substantial antitumor mechanism has been researched , little has focused on its enantiomer (+)-Zeylenone.This article will try to find a gram scale synthesis method of (+)-Zeylenone and explain the structure-activity relationship of this kind of compound. Total synthesis of (+)-zeylenone was completed in 13 steps with quinic acid as starting material in 8.8% overall yield. The highlight of the route was the control of the three carbon’s chirality by clever use of single step dihydroxylation under the direction of the key C-3 chirality. In addition, zeylenone derivatives were designed and synthesized and their antitumor activity were evaluated against three human cancer cell lines using the CCK8 assay. Structure-activity relationship suggested compounds with both two absolute configurations exhibited good activity. Besides, hydroxyls at C-1/2 position were crucial for the activity and esterification of C-1 hydroxyl with large groups made the activity disappeared. Hydroxyl at C-3 position was also important as proper ester substituent could increase the potency.


1995 ◽  
Vol 43 (9) ◽  
pp. 1598-1600 ◽  
Author(s):  
Motomasa KOBAYASHI ◽  
Weiqi WANG ◽  
Naoki OHYABU ◽  
Michio KUROSU ◽  
Isao KITAGAWA

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