Tandem semipinacol/Schmidt reaction leading to a versatile and efficient approach to azaquaternary alkaloid skeletons.
[Structure: see text] A TiCl4-promoted tandem semipinacol/Aubé's type intramolecular Schmidt reaction of alpha-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.
Gu
Peiming
P
State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PRC.
Zhao
Yu-Ming
YM
Tu
Yong Qiang
YQ
Ma
Yufei
Y
Zhang
Fumin
F