Tandem Semipinacol/Schmidt Reaction Leading to a Versatile and Efficient Approach to Azaquaternary Alkaloid Skeletons

Tandem Semipinacol/Schmidt Reaction Leading to a Versatile and Efficient Approach to Azaquaternary Alkaloid Skeletons

A TiCl4-promoted tandem semipinacol/Aubé's type intramolecular Schmidt reaction of α-siloxy-epoxy-azide has been designed and developed to be a general method for efficient construction of azaquaternary carbon units. As applicable examples, some key tricyclic azaquaternary skeletons incorporate...

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Veröffentlicht in:Organic letters 2006-11, Vol.8 (23), p.5271-5273
Hauptverfasser: Gu, Peiming, Zhao, Yu-Ming, Tu, Yong Qiang, Ma, Yufei, Zhang, Fumin
Format: Artikel
Sprache:eng
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Zusammenfassung:A TiCl4-promoted tandem semipinacol/Aubé's type intramolecular Schmidt reaction of α-siloxy-epoxy-azide has been designed and developed to be a general method for efficient construction of azaquaternary carbon units. As applicable examples, some key tricyclic azaquaternary skeletons incorporated in many important alkaloids, such as cephalotaxine, stemonamine, erythrinan, and homoerythrinan alkaloids, have been constructed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062116r