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General approach for the total synthesis of the sarpagine related indole alkaloids (+)-Na-methyl-16-epipericyclivine, (−)-alkaloid Q3 and (−)-panarine via the asymmetric Pictet–Spengler reaction

✍ Scribed by Jianming Yu; Xiangyu Z Wearing; James M Cook

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
136 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 rotation {[h] D 0 (c 0.50, CHCl 3 )} was biogenetically unreasonable. The first total synthesis of (-)-alkaloid Q 3 ( 5) and (-)-panarine (6), via the intermediate vellosimine (18), is also described.

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