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. 2010 Oct 6;132(39):13642-4.
doi: 10.1021/ja1057828.

Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K

Ji Qi  1 , Aaron B Beeler, Qiang Zhang, John A Porco Jr
Affiliations

Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K

Ji Qi et al. J Am Chem Soc. .

Abstract

The asymmetric total synthesis of the polyprenylated acylphloroglucinol hyperibone K has been achieved using an enantioselective alkylative dearomatization-annulation process. NMR and computational studies were employed to probe the mode of action of a chiral phase-transfer (ion pair) catalyst.

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Figures

Figure 1
Figure 1
Polyisoprenylated Acylphloroglucinol Natural Products
Figure 2
Figure 2
Dearomatization/Alkylation Using Cinchona Alkaloid-Derived Catalysts Using Various Phase Transfer Catalysts
Figure 3
Figure 3
Determination of the Absolute Configuration of 5
Figure 4
Figure 4
Allylic Cation Intermediate 13
Figure 5
Figure 5
Dearomatized Acyl Phloroglucinols 14–17
Figure 6
Figure 6
Optimized Conformation of Catalyst 8e with Key nOe’s
Figure 7
Figure 7
Proposed Binding Model of Catalyst 8e and 15. a) Key interactions of 8e and 15. b) 1.4 Å Connolly surface.
Scheme 1
Scheme 1
Retrosynthetic Analysis for Hyperibone K
Scheme 2
Scheme 2
Total Synthesis of (−)-Hyperibone K
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References

    1. Ito C, Itoigawa M, Miyamoto Y, Onoda S, Rao KS, Mukainaka T, Tokuda H, Nishino H, Furukawa H. J Nat Prod. 2003;66:206–209. - PubMed
    1. Piccinelli AL, Cuesta-Rubio O, Chica MB, Mahmood N, Pagano B, Pavone M, Barone V, Rastrelli L. Tetrahedron. 2005;61:8206–8211.
    1. Tanaka N, Takaishi Y, Shikishima Y, Nakanishi Y, Bastow K, Lee KH, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O. J Nat Prod. 2004;67:1870–1875. - PubMed
    1. Henry GE, Jacobs H, Sean Carrington CM, McLean S, Reynolds WF. Tetrahedron Lett. 1996;37:8663–8666.
    1. Rodeschini V, Simpkins NS, Wilson C. J Org Chem. 2007;72:4265–4267. - PubMed

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