Catalytic asymmetric synthesis of descurainin via 1,3-dipolar cycloaddition of a carbonyl ylide using Rh2(R-TCPTTL)4

TETRAHEDRON LETTERS

卷:51

Article

Shimada, Naoyuki¹  Hanari, Taiki¹  Kurosaki, Yasunobu¹  Anada, Masahiro¹  Nambu, Hisanori¹  Hashimoto, Shunichi¹ 

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

关键词: Carbonyl ylide;    1,3-Dipolar cycloaddition;    Chiral dirhodium(II) catalyst;    Descurainin;   

DOI  :  10.1016/j.tetlet.2010.10.036

来源: Elsevier

【 摘 要 】

A catalytic asymmetric synthesis of descurainin has been achieved by incorporating an enantioselective 1,3-dipolar cycloaddition, a stereoselective alkene hydrogenation, an oxidation with Fremy's salt and a regioselective demethylation with NbCl5 as the key step. The 1,3-dipolar cycloaddition of a carbonyl ylide derived from tert-butyl 2-diazo-5-formyl-3-oxopetanoate with 4-hydroxy-3-methoxyphenylacetylene in the presence of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinate], Rh-2(R-TCPTTL)(4), provided an 8-oxabicyclo[3.2.1]octane skeleton in 95% ee. (C) 2010 Elsevier Ltd. All rights reserved.

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