Facile Synthesis of Pyrano[3,2-e]indoles via the Base-Promoted Pictet-Spengler Reaction of Nb-Benzylserotonin
โ Scribed by Ishikura, Minoru; Yamada, Koji; Yamaguchi, Sayaka; Hatae, Noriyuki; Abe, Takumi; Iwamura, Tatsunori
- Book ID
- 118272873
- Publisher
- Japan Institute of Heterocyclic Chemistry
- Year
- 2011
- Tongue
- English
- Weight
- 806 KB
- Volume
- 83
- Category
- Article
- ISSN
- 0385-5414
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๐ SIMILAR VOLUMES
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.
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