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. 2014 Mar 26;136(12):4504-7.
doi: 10.1021/ja501780w. Epub 2014 Mar 12.

Total synthesis of the akuammiline alkaloid picrinine

Joel M Smith  1 , Jesus Moreno, Ben W Boal, Neil K Garg
Affiliations

Total synthesis of the akuammiline alkaloid picrinine

Joel M Smith et al. J Am Chem Soc. .

Abstract

We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.

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Figures

Figure 1
Figure 1
Representative akuammiline alkaloids 1–6.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
See this image and copyright information in PMC

References

    1. For reviews on akuammiline alkaloids, see:

    2. Ramírez A.; García–Rubio S. Curr. Med. Chem. 2003, 10, 1891–1915. - PubMed
    3. Eckermann R.; Gaich T. Synthesis 2013, 45, 2813–2823.
    1. For the initial isolation of 1, see:Group-Besanez v. Justus Liebigs Ann. Chem. 1875, 176, 88–89.
    1. For the isolation of 2, see:Subramaniam G.; Hiraku O.; Hayashi M.; Koyano T.; Komiyama K.; Kam T.-S. J. Nat. Prod. 2007, 70, 1783–1789. - PubMed
    1. For the initial isolation of 3, see:Mokŕý J.; Dúbravková L.; Šefčovič P. Experientia 1962, 18, 564–565. - PubMed
    1. For the isolation of 4, see:Cai X.-H.; Tan Q.-G.; Liu Y.-P.; Feng T.; Du Z.-Z.; Li W.-Q.; Luo X.-D. Org. Lett. 2008, 10, 577–580. - PubMed

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