1193374-92-3Relevant academic research and scientific papers
Intermediate for preparing halichondrin compound and preparation method thereof
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Paragraph 0132; 0171-0173, (2020/07/07)
The invention relates to an intermediate for preparing a halichondrin compound and a preparation method thereof. The invention particularly relates to an intermediate for preparing halichondrin, eribulin or analogues thereof, and a preparation method and application of the intermediate. The intermediate as well as the preparation method and application thereof are used for constructing C20-C26 structural fragments of the halichondrin compound. The initial raw materials of the synthesis route are cheap, easy to obtain, stable in source and reliable in quality; the structural characteristics ofreactants are fully utilized in the selection of a chiral center construction method, so that the synthesis efficiency is practically improved, and the difficulty and risk of product quality control are reduced; and the use of a high-toxicity and expensive organic tin catalyst is avoided, so that the cost and the environmental friendliness are remarkably improved.
SYNTHESIS OF HALICHONDRIN ANALOGS AND USES THEREOF
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Paragraph 00306, (2016/01/25)
The present invention provides halichondrin analogs, such as compounds of Formula (I). The compounds may bind to microtubule sites, thereby inhibiting microtubule dynamics. Also provided are methods of synthesis, pharmaceutical compositions, kits, methods
Total synthesis of halichondrin A, the missing member in the halichondrin class of natural products
Ueda, Atsushi,Yamamoto, Akihiko,Kato, Daisuke,Kishi, Yoshito
supporting information, p. 5171 - 5176 (2014/04/17)
A total synthesis of halichondrin A, the phantom member in the halichondrin class of natural products, is reported. The highlights of synthesis include: (1) synthesis of C1-C19 building block 6b via a catalytic asymmetric Cr-mediated coupling of 12 and 13b; (2) synthesis of the right-half of 19 via an asymmetric Ni/Cr-mediated coupling, followed by base-induced furan formation, and Shiina macrolactonization; (3) synthesis of enone 20 via Ni/Cr-mediated coupling of 5 with 19, followed by oxidation; (4) synthesis of halichondrin A from 20, with use of a newly discovered, highly selective TMSOTf-mediated equilibration of C38-epi-halichondrin A to halichondrin A. Two pieces of evidence are presented unambiguously to establish the structure of halichondrin A thus synthesized: one is the synthesis of norhalichondrin A (24) from 19 and 23, and the other is the study of the proton chemical shift difference between synthetic halichondrin A and known members of this class of natural products.
New syntheses of E7389 C14-C35 and halichondrin C14-C38 building blocks: Reductive cyclization and oxy-Michael cyclization approaches
Dong, Cheng-Guo,Henderson, James A.,Kaburagi, Yosuke,Sasaki, Takeo,Kim, Dae-Shik,Kim, Joseph T.,Urabe, Daisuke,Guo, Haibing,Kishi, Yoshito
supporting information; experimental part, p. 15642 - 15646 (2010/01/29)
Cr-mediated coupling reactions are usually achieved with a slight excess of a given nucleophile. To develop a cost-effective use of this process, two different approaches have been studied. The first approach depends on two consecutive catalytic asymmetri
