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. 2013 Feb 13;54(7):635-637.
doi: 10.1016/j.tetlet.2012.11.135.

Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V

Kiel E Lazarski  1 , Berkcan Akpinar, Regan J Thomson
Affiliations

Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V

Kiel E Lazarski et al. Tetrahedron Lett. .

Abstract

Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry.

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Figures

Figure 1
Figure 1
Our previous report towards maoecrystal V (3).
Figure 2
Figure 2
Previous C–H functionalization attempts (P = TBS).
Figure 3
Figure 3
C–H functionalization attempts in the absence of the nitro group (P = TBS).
Figure 4
Figure 4
Possible mechanism for the formation of 10 and 11.
Figure 5
Figure 5
Simplified C–H functionalization model system.
Figure 6
Figure 6
An alternative “east-to-west” strategy (P = TBS).
See this image and copyright information in PMC

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References

    1. Sun HD, Huang SX, Han QB. Nat. Prod. Rep. 2006;23:673–698. - PubMed
    1. Gong J, Lin G, Li CC, Yang Z. Org. Lett. 2009;11:4770–4773. - PubMed
    2. Krawczuk PJ, Schöne N, Baran PS. Org. Lett. 2009;11:4774–4776. - PMC - PubMed
    3. Peng F, Yu M, Danishefsky SJ. Tetrahedron Lett. 2009;50:6586–6587. - PMC - PubMed
    4. Nicolaou KC, Dong L, Deng L, Talbont AC, Chen DY-K. Chem. Comm. 2010;46:70–72. - PubMed
    5. Singh V, Bhalerao P, Movin SM. Tetrahedron Lett. 2010;51:3337–3339.
    6. Lazarski KE, Hu DX, Stern CL, Thomson RJ. Org. Lett. 2010;12:3010–3013. - PMC - PubMed
    7. Baitinger I, Mayer P, Trauner D. Org. Lett. 2010;12:5656–5659. - PubMed
    8. Peng F, Danishefsky SJ. Tetrahedron Lett. 2011;52:2104–2106. - PMC - PubMed
    9. Gu Z, Zakarian A. Org. Lett. 2011;13:1080–1082. - PMC - PubMed
    10. Dong L, Deng L, Lim YH, Leung GYC, Chen DY-K. Chem. Eur. J. 2011;17:5887–5781. - PubMed
    1. Gong J, Lin G, Sun W, Li CC, Yang Z. J. Am. Chem. Soc. 2010;132:16745–16746. - PubMed
    2. Peng F, Danishefsky SJ. J. Am. Chem. Soc. Article ASAP.

    1. For relevant reviews of remote functionalization reactions, see: Heusler K, Kalvoda J. Angew. Chem. Int. Ed. 1964;3:525–596. Godula K, Sames D. Science. 2006;312:67–72. Brückl T, Baxter RD, Ishihara Y, Baran PS. Acc. Chem. Res. 2012;45:826–839.

    1. Miller RD, McKean DR. Synthesis. 1979:730–732.

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