Tandem semipinacol/Schmidt reaction leading to a versatile and efficient approach to azaquaternary alkaloid skeletons |
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| Authors: | Gu Peiming Zhao Yu-Ming Tu Yong Qiang Ma Yufei Zhang Fumin |
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| Institution: | State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PRC. |
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| Abstract: | 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. |
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