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. 2008 Nov 6;10(21):4955-7.
doi: 10.1021/ol802041c. Epub 2008 Oct 10.

A concise and modular synthesis of pyranicin

Nolan D Griggs  1 , Andrew J Phillips
Affiliations

A concise and modular synthesis of pyranicin

Nolan D Griggs et al. Org Lett. .

Abstract

A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.

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Figures

Figure 1
Figure 1
Pyranicin and overall synthesis strategy.
Scheme 1
Scheme 1
Synthesis of the C7–C32 pyran-containing domain.
Scheme 2
Scheme 2
Synthesis of the butenolide domain and completion of the synthesis.
See this image and copyright information in PMC

References

    1. For a review see: Bermejo A, Figadere B, Zafra-Polo M-C, Barrachina I, Estornell E, Cortes D. Nat Prod Rep. 2005;22:269. and references cited therein.

    1. Alali FQ, Rogers L, Zhang Y, McLaughlin JL. Tetrahedron. 1998;54:5833.
    1. Keaton KA, Phillips AJ. J Am Chem Soc. 2006;128:408. - PubMed

    1. For other total syntheses see: Strand D, Norrby PO, Rein T. J Org Chem. 2006;71:1879.Strand D, Rein T. Org Lett. 2005;7:199.Takahashi S, Kubota A, Nakata T. Org Lett. 2003;5:1353.Hattori Y, Furuhata S-i, Okajima M, Konno H, Abe M, Miyoshi H, Goto T, Makabe H. Org Lett. 2008;10:717.Furuhata S-i, Hattori Y, Okajima M, Konno H, Abe M, Miyoshi H, Goto T, Makabe H. Tetrahedron. 2008;64:7695.

    1. Henderson JA, Jackson KL, Phillips AJ. Org Lett. 2007;9:5299.Um JM, Houk KN, Phillips AJ. Org Lett. 2008;10:3769.See also Nicolaou KC, Frederick MO, Burtoloso ACB, Denton RM, Rivas F, Cole KP, Aversa RJ, Gibe R, Umezawa T, Suzuki TJ. Am Chem Soc. 2008;130:7466.

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