Citation: De Gang Liu, Ji Jun Xue, Zhi Xiang Xie, Li Ping Wei, Hua Bing Zhang, Ying Li. Asymmetric synthesis of pedamide using I₂-induced heterocyclization to construct the skeleton[J]. Chinese Chemical Letters, ;2009, 20(7): 775-778. doi: 10.1016/j.cclet.2009.03.026 shu

Asymmetric synthesis of pedamide using I₂-induced heterocyclization to construct the skeleton

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China

Received Date: 17 October 2008

Fund Project: We are grateful for the financial support of the National Natural Science Foundation of China (No.20672050).

An alternative approach to synthesize pedamide, a key building block of pederin was described. Iodine-induced asymmetric heterocyclization was used as the key step to construct the skeleton, a tetrahydropyran ring with three chiral centers. Brown's asymmetric allylation and Lewis acid-mediated allylation were investigated to introduce chains and chiral alcohols. Sharpless dihydroxylation decorated the side chain. And high optically pure target was obtained by removing the epimers formed in these reactions on column chromatography.
- Synthesis,
- Pedamide,
- PederinReferences
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