Total syntheses of squamocin A and squamocin D
โ Scribed by Ulrich Emde; Ulrich Koert
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 197 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The total syntheses of two acetogenins, squamocin A and squamocin D, have been achieved. The adjacent bis-THF subunit was constructed by a multiple Williamson reaction. The left and the right side chain were added by addition of organomagnesium compounds to aldehyde functions. The conversion of a carboxylic acid into the butenolide moiety concluded both syntheses.
๐ SIMILAR VOLUMES
The total syntheses of the Annonaceous acetogenins squamocin A and squamocin D have been achieved. The synthesis follows a modular strategy, wherein a left-side chain, the central bis-THF core and the right-side chain are assembled together. Key reactions are additions of organomagnesium
Comtxmnd 1 was synthesized in 9 steps and 5.5% overall yield lrom heptanal. The IC50 of comlxmnd 1 against tile growth of human hepatocarcinoma cell lines (Hep G2 and 2,2,15) are 22.0 and 21.8 p3vl, respectively.