General Approach for the Synthesis of 12-Methoxy-Substituted Sarpagine Indole Alkaloids Including (-)-12-Methoxy-N b-methylvoachalotine,(+)-12-Methoxy-N a- …

H Zhou, X Liao, W Yin, J Ma…

Index: Zhou, Hao; Liao, Xuebin; Yin, Wenyuan; Ma, Jun; Cook, James M. Journal of Organic Chemistry, 2006 , vol. 71, # 1 p. 251 - 259

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Citation Number: 44

Abstract

The enantiospecific synthesis of 7-methoxy-d-tryptophan ethyl ester was completed by combination of the Larock heteroannulation process with a Schöllkopf-based chiral auxiliary in good yield. This ester was then employed in the first regiospecific, stereospecific total synthesis of (+)-12-methoxy-N a-methylvellosimine,(+)-12-methoxyaffinisine,(-)- fuchsiaefoline, and 12-methoxy-N b-methylvoachalotine in excellent overall yield. The ...