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Approach Toward the Total Synthesis of Lundurines

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New Gold-Catalyzed Reactions and Applications for the Synthesis of Alkaloids

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Abstract

The methodology developed in the A-D group for the gold-catalyzed cyclization of indoles with alkynes was applied in the total synthesis of lundurines. Lundurines are a new type of alkaloids characterized by a cyclopropyl fragment embedded within a hexacyclic ring system that includes a 1H–azocine[5,4–b]indole ring unit. The key step in the total synthesis of lundurine A is a 8–endo–dig cyclization of the alkynylindole catalyzed by AuCl3, which affords exclusively the desired azocine[5,4–b]indole derivative.

Part of these results have been published in: Ferrer, C., Escribano-Cuesta, A., Echavarren, A. M.: Tetrahedron, 65, 9015–9020 (2009).

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Notes

  1. 1.

    Lead references on indole alkaloids form genus Kopsia: Subramaniam et al. [33, 34], Kam et al. [35], Awang et al. [36].

  2. 2.

    General review about cyclopropanation: Lebel et al. [58].

  3. 3.

    General review about indole cyclopropanation: Zhang et al. [59].

  4. 4.

    General review about conversion of carbonyl compounds to alkynes: Habrant et al. [60].

  5. 5.

    General reviews about metal-catalyzed approaches to amide bond formation: Joullié and Lassen [61], Allen and Williams [62].

  6. 6.

    First example of synthesis and reactivity of pyrrole-based silyl dienol ether: Fiorenza et al. [85].

  7. 7.

    Selected reviews: Rassu et al. [86, 87].

  8. 8.

    Synthesis and γ-alkylation of pyrrole-based silyl dienol ether: Zanardi et al. [88].

  9. 9.

    III-47 can be synthesized by Ireland-Claisen ester rearrangement but only on small scale: Kazmaier et al. [126], Chandan and Moloney [127].

  10. 10.

    The reported ee of III-47 was determined via conversion of the final product to the Mosher amide under Schotten-Bauman conditions [121]. The desired product was observed as a single peak, >99 % diasteromerically pure.

  11. 11.

    First example for the oxidation of cyclic amines with ruthenium tetraoxide: Sheehan and Tulis [136], Yoshifuji et al. [137, 138], Tanaka et al. 139].

  12. 12.

    In this part of the chapter, only the methodology that allowed the connection of both fragments is discussed. All of the previous attempts are discussed in the 3.3.4 Annex.

  13. 13.

    Reviews about metal-catalyzed coupling reaction: Dehli et al. [142], Evano et al. [143].

  14. 14.

    Synthesis of enamides starting from 2-pyrrolidine and vinyl triflates: Wallace et al. [147], Klapars et al. [148]. From vinyl chlorides: Hesse and Kirsch [149].

  15. 15.

    For the synthesis of N-acyl vinylogous carbamic acids and ureas see: Han et al. [151].

  16. 16.

    Selected examples for the copper-catalyzed cross-coupling of lactam and heteroaryl vinyl halides: Sun et al. [155], Meketa and Weinreb [156, 157], Yang et al. [158].

  17. 17.

    Optimizated conditions for the copper-catalyzed cross-coupling of protected maleimide hemianals: Coleman and Liu [162].

  18. 18.

    Pioneer examples of ruthenium complexes, which mediate the addion of certain amides to terminal alkynes: Heider et al. [185], Kondo et al. [186].

  19. 19.

    See general review: DeKorver et al. [196].

  20. 20.

    For alkynyl bromides: Zhang et al. [201], Yao et al. [202].

  21. 21.

    For 1,1-dibromo-1-alkene: Coste et al. 203].

  22. 22.

    General review about α-arylation of electron-rich olefins: Ruan and Xiao [213].

  23. 23.

    General review about palladium-catalyzed coupling reactions of aryl chlorides: Littke and Fu [217].

  24. 24.

    First example of the Heck reaction using aryl chlorides and P(t-Bu)3 as ligand: Littke and Fu [218].

  25. 25.

    Hermann's palladacycle is characterized by a high termal stability, prermitting it to be used with low cost, but poorly reactive, aryl chloride substrates. General review about application of palladacyles in Heck type reactions: Herrmann et al. [221].

  26. 26.

    [(t-Bu3)PH]BF4 is used as an air-stable preligand of P(t-Bu)3.

  27. 27.

    The analogous N-vinyl pyrrolidine of lactam III-53 could be synthesized by palladium(II)-catalyzed vinyl tranfer from vinyl ethers: Brice et al. [230].

  28. 28.

    Complete β-regioselective Heck reaction has been reported using tert-butyl 3-iodo-1H-indole-1-carboxylate (III-62Boc) with electron-poor alkenes: Yue and Larock [231], Yue et al. [232], Putey et al. [233], Mitsudo et al. [234], Della Sala et al. [235].

  29. 29.

    Complete β-regioselective Heck reaction has been reported using tert-butyl 3-bromo-1H-indole-1-carboxylate (III-73) with electron-poor and -neutral alkenes: Busacca and Dong [236], Omura et al. [237], Hussain et al. 238].

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    Ana Escribano Cuesta

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Escribano Cuesta, A. (2013). Approach Toward the Total Synthesis of Lundurines. In: New Gold-Catalyzed Reactions and Applications for the Synthesis of Alkaloids. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-00702-1_4

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