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Issue 31, 2015
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Concise diastereoselective synthesis of calcaripeptide C via asymmetric transfer hydrogenation/Pd-induced chiral allenylzinc as a key reaction

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Abstract

Synthesis of the natural product calcaripeptide C derived from the fungal metabolite mycelium KF525 of Calcarisporium sp. has been achieved. This complementary approach avoids the use of a stoichiometric amount of chiral auxiliary reagents as commonly used to generate enantioenriched advanced precursors. The enantioselective synthesis of calcaripeptide C is remarkable in that using catalytic reactions sets the two stereogenic centers efficiently with good levels of enantioselectivity. Further diversification of the calcaripeptide C structures is possible by employing a complementary catalytic enantioenriched Ru-catalyst.

Graphical abstract: Concise diastereoselective synthesis of calcaripeptide C via asymmetric transfer hydrogenation/Pd-induced chiral allenylzinc as a key reaction

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Publication details

The article was received on 09 Jun 2015, accepted on 30 Jun 2015 and first published on 30 Jun 2015


Article type: Paper
DOI: 10.1039/C5OB01164G
Citation: Org. Biomol. Chem., 2015,13, 8487-8494
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    Concise diastereoselective synthesis of calcaripeptide C via asymmetric transfer hydrogenation/Pd-induced chiral allenylzinc as a key reaction

    G. Kumaraswamy, V. Narayanarao and R. Raju, Org. Biomol. Chem., 2015, 13, 8487
    DOI: 10.1039/C5OB01164G

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