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General Approach for the synthesis of macroline/sarpagine related indole alkaloids Via the asymmetric pictet-spengler reaction: the enantiospecific synthesis of the Na-H, azabicyclo[3.3.1]nonone template

✍ Scribed by Yu Peng; Tao Wang; Yu Fuxiang; James M. Cook


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
198 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


Na-H, Nb-benzyltetracyclic ketone la, a potential intermediate for the synthesis of numerous sarpagine-related alkaloids, has been synthesized enantiospecifically from D-( + )tryptophan via the asymmetric Pictet-Spengler reaction.


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General approach for the total synthesis
✍ Jianming Yu; Xiangyu Z Wearing; James M Cook πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 136 KB

The stereospecific total synthesis of (+)-N a -methyl-16-epipericyclivine (1) was completed [from D-(+)-tryptophan methyl ester] in an overall yield of 42% (eight reaction vessels). The optical rotation {[h] D +22.8 (c 0.50, CHCl 3 )} obtained on this material confirmed that the reported optical rot