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Synthesis 2016; 48(23): 4110-4116
DOI: 10.1055/s-0035-1561494
DOI: 10.1055/s-0035-1561494
paper
Concise Preparation of the Bis-THF Core of Annonaceous Acetogenins
Weitere Informationen
Publikationsverlauf
Received: 10. Mai 2016
Accepted after revision: 09. Juni 2016
Publikationsdatum:
26. Juli 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201623/lookinside/thumbnails/ss-2016-m0333-op_10-1055_s-0035-1561494-1.jpg)
Abstract
A concise preparation of the all-(R) threo/trans/threo/ trans/threo bis-THF core present in natural acetogenins is presented. Starting from a terminal alkene, homometathesis and two consecutive stereoselective cyclizations afforded the bis-THF core through a short and efficient sequence. In addition, the isomeric erythro/trans/ threo/trans/erythro bis-THF core was also synthesized in high yield. The starting alkene was previously prepared from a homochiral cis-diol derived from biotransformation of bromobenzene.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561494.
- Supporting Information
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For examples of bis-THF acetogenins displaying the all-R threo/trans/threo/trans/threo motif, see: Asimicin:
Squamocin-K, F, and D:
Parviflorin:
Annonisin and asiminocin:
Longimicin-A, B, C, and D:
Glaucanetin:
Asimin, asiminacin, and asiminecin:
Bullacin-B:
Uvarigrandin-A:
Calamistrin-F:
Asimicinone:
Tucumanin.: