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Issue 32, 2016
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Synthesis of the 2-formylpyrrole spiroketal pollenopyrroside A and structural elucidation of xylapyrroside A, shensongine A and capparisine B

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Abstract

A convergent synthesis of the 2-formyl pyrrole spiroketal pollenopyrroside A is reported. The key step involves a Maillard-type condensation of an amine derived from deoxy-D-ribose with a dihydropyranone to furnish the 2-formylpyrrole ring system. Spectroscopic and physical data of 9-epi-pollenopyrroside A are also provided, elucidating the structures of the previously isolated 2-formylpyrrole spiroketals capparisine B, shensongine A and xylapyrroside A.

Graphical abstract: Synthesis of the 2-formylpyrrole spiroketal pollenopyrroside A and structural elucidation of xylapyrroside A, shensongine A and capparisine B

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Publication details

The article was received on 24 Jun 2016, accepted on 20 Jul 2016 and first published on 20 Jul 2016


Article type: Paper
DOI: 10.1039/C6OB01361A
Citation: Org. Biomol. Chem., 2016,14, 7659-7664
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    Synthesis of the 2-formylpyrrole spiroketal pollenopyrroside A and structural elucidation of xylapyrroside A, shensongine A and capparisine B

    J. M. Wood, D. P. Furkert and M. A. Brimble, Org. Biomol. Chem., 2016, 14, 7659
    DOI: 10.1039/C6OB01361A

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