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. 2010 Feb 1;49(6):1095-8.
doi: 10.1002/anie.200907112.

Total synthesis of palau'amine

Ian B Seiple  1 , Shun Su, Ian S Young, Chad A Lewis, Junichiro Yamaguchi, Phil S Baran
Affiliations

Total synthesis of palau'amine

Ian B Seiple et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
Selected pyrrole-imidazole alkaloids, and retrosynthetic analysis of palau’amine (1). Ar = 2-(4,5-dibromopyrrole).
Scheme 1
Scheme 1
Total synthesis of palau’amine (1). Counterions are CF3CO2− and are omitted for clarity. Reagents and conditions: a) TFA/H2O (1/1), 50 °C, 12 h, then silver(II)picolinate (2.4 equiv), TFA/H2O (1/9), 23 °C, 5 min, 64% + 17% recovered 8; b) H2NCN (40 equiv), pH 5, brine, 70 °C, 4 h, 65%; c) TFAA/TFA (1/1), 1 h, then Br2 (2.0 equiv), 1 h, then TFA/H2O (1/1) 1 h, 38 °C, 54%; d) AcOH (3.0 equiv), 12 (3.0 equiv), THF, 38 °C, 6 h, then TFA/DCM (1/30 to 1/1), 23 °C, 12 h, 44%; e) Pd(OAc)2 (1.6 equiv), H2 (bubbled through solution) TFA/H2O (1/9), 23 °C, then EDC (2.8 equiv), HOBt (2.8 equiv), DMF, 23 °C, 3 h, then TFA, 70 °C, 38 h, 17% from 5. TFA = trifluoroacetic acid, TFAA = trifluoroacetic anhydride, THF = tetrahydrofuran, HOBt = N-hydroxybenzotriazole, EDC = 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, DMF = N,N-dimethylformamide.
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Comment in

References

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