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Enantiospecific total synthesis of the enantiomer of the indole alkaloid intermediate macroline

✍ Scribed by Xiaoxiang Liu; Chunchun Zhang; Xuebin Liao; James M. Cook

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
172 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The total synthesis of the enantiomer 3En of macroline 3 was completed (from L-tryptophan methyl ester 6) in an overall yield of 12.3% (11 isolated intermediates). The corresponding macroline equivalent 18 was prepared in 14.3% yield. This work provides, for the first time, an opportunity to synthesize mismatched bisindole alkaloids for studies on the mechanism of action of Alstonia antimalarial alkaloids at the receptor level.

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