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Fuwa H Suzuki T Kubo H Yamori T Sasaki M 《Chemistry (Weinheim an der Bergstrasse, Germany)》2011,17(9):2678-2688
We describe herein an enantioselective total synthesis of (-)-exiguolide, the natural enantiomer. The methylene bis(tetrahydropyran) substructure was efficiently synthesized by exploiting olefin cross-metathesis for the assembly of readily available acyclic segments and intramolecular oxa-conjugate cyclization and reductive etherification for the formation of the tetrahydropyran rings. The 20-membered macrocyclic framework was constructed in an efficient manner by means of Julia-Kocienski coupling and Yamaguchi macrolactonization. Finally, the (E,Z,E)-triene side chain was introduced stereoselectively via Suzuki-Miyaura coupling to complete the total synthesis. Assessment of the growth inhibitory activity of synthetic (-)-exiguolide against a panel of human cancer cell lines elucidated for the first time that this natural product is an effective antiproliferative agent against the NCI-H460 human lung large cell carcinoma and the A549 human lung adenocarcinoma cell lines. Moreover, we have investigated structure-activity relationships of (-)-exiguolide, which elucidated that the C5-methoxycarbonylmethylidene group and the length of the side chain are important for the potent activity. 相似文献
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Total synthesis of (+)-batzelladine A and (-)-batzelladine D, and identification of their target protein 总被引:1,自引:0,他引:1
Shimokawa J Ishiwata T Shirai K Koshino H Tanatani A Nakata T Hashimoto Y Nagasawa K 《Chemistry (Weinheim an der Bergstrasse, Germany)》2005,11(23):6878-6888
Asymmetric total synthesis of batzelladine A (1) and batzelladine D (2) has been achieved. Our synthesis of batzelladines features 1) stereoselective construction of the cyclic guanidine system by means of successive 1,3-dipolar cycloaddition reaction and subsequent cyclization, 2) direct esterification of the bicyclic carboxylic acid 35 with the guanidine alcohol 8 or 59 to construct the whole carbon skeleton of batzelladines, and 3) one-step formation of the alpha,beta-unsaturated aldehyde 53 from the primary alcohol 47 with tetra-n-propylammoniumperruthenate (TPAP), providing an efficient route to the left-hand bicyclic guanidine alcohol of batzelladine A (1). With the synthetic compounds 1 and 2 in hand, their target protein was examined by using immobilized CD4 and gp120 affinity gels. The results indicated that batzelladines A (1) and D (2) bind specifically to CD4. 相似文献
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Total synthesis of gambierol: subunit coupling and completion 总被引:2,自引:0,他引:2
Johnson HW Majumder U Rainier JD 《Chemistry (Weinheim an der Bergstrasse, Germany)》2006,12(6):1747-1753
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