Citation: Pei Ming Gu, Yu Ming Zhao, Yong Qiang Tu, Min Wang, Shu Yu Zhang. An alternative synthetic approach towards erythrinan and homoerythrinan alkaloids by tandem semipinacol/intramolecular Schmidt reaction[J]. Chinese Chemical Letters, ;2007, 18(8): 917-919. doi: 10.1016/j.cclet.2007.05.029 shu

An alternative synthetic approach towards erythrinan and homoerythrinan alkaloids by tandem semipinacol/intramolecular Schmidt reaction

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

Received Date: 4 January 2007

Fund Project: We gratefully acknowledge financial support from the NNSFC (Nos. 30271488 and 20021001) and the Chang Jiang Scholars Program.

An alternative construction of A-B-D ting-system of erythrinan and homoerythrinan alkaloids by TiCl₄-mediated tandem semipinacol/intramolecular Schmidt reaction of α-siloxyepoxyazide was addressed and the unusual epoxidation stereoselectivity was observed in preparation of the substrate once again.
- Tandem,
- Intramolecular Schmidt reaction,
- Semipinacol,
- Alkaloid
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2. [2]
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