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Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine

✍ Scribed by Xiaoxiang Liu; Tao Wang; Qingge Xu; Chunrong Ma; James M Cook

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
189 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

The enantiomer of anisine has been synthesized (from l-tryptophan) with 100% diastereoselectivity via the asymmetric PictetΒ±Spengler reaction coupled with a Pd 0 (enolate mediated) coupling process. This enantiomer has also been converted into a key intermediate which provides a route to the enantiomers of both macroline and alstonerine following the previous work of LeQuesne.

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✍ Xiaoxiang Liu; Chunchun Zhang; Xuebin Liao; James M. Cook πŸ“‚ Article πŸ“… 2002 πŸ› Elsevier Science 🌐 French βš– 172 KB

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 synthes

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The tetrahedrane framework with R=tBu and the octabisvalene framework with R = CH3 presumably form because of steric reasons. Whereas the hydrocarbon 2 is highly strained, the arrangement in 1 is largely strain-free, based on the intermolecular contact distances. With other residues R the occurrenc