期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 40, 页码 14052-14054出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja1070043
关键词
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资金
- NSFC [20772083, 20825207, 21021001]
- PCSIRT [IRT0846]
- National Basic Research Program of China [2010CB833200]
- State Key Laboratory of Bioorganic and Natural Products Chemistry
- Shanghai Institute of Organic Chemistry
The first asymmetric total synthesis of (+)-perophoramidine has been achieved in 17 steps with similar to 11% overall yield. The key step relies on an asymmetric biomimetic Die Is Alder reaction between the in situ-generated chiral diene T-24 and the substituted tryptamine 23 to assemble the core structure 27a in a highly efficient way. An acid-catalyzed thermodynamic equilibrium results in C=N double-bond migration of the amidine moiety in 37, which guarantees a regioselective methylation on NI at the end of the synthesis. The absolute configuration of (+)-perophoramidine was determined by X-ray crystallographic analysis of the chiral intermediate 32 and comparison of the rotation of synthetic (+)-perophoramidine with that of the natural product.
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