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Issue 39, 2015
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Racemic total synthesis of dactyloidin and demethyldactyloidin through the DL-proline-catalyzed Knoevenagel condensation/[4 + 2] cycloaddition cascade

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Abstract

An efficient approach towards the first racemic total synthesis of dactyloidin (2) and demethyldactyloidin (3) is described. Their oxygen-bridged tricyclic ketal systems were rapidly constructed by using a remarkable biomimetic Knoevenagel condensation/[4 + 2] cycloaddition cascade as the critical strategy and the 1,5-dicarbonyl segment was assembled by Grignard addition.

Graphical abstract: Racemic total synthesis of dactyloidin and demethyldactyloidin through the dl-proline-catalyzed Knoevenagel condensation/[4 + 2] cycloaddition cascade

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Publication details

The article was received on 06 Aug 2015, accepted on 13 Aug 2015 and first published on 13 Aug 2015


Article type: Paper
DOI: 10.1039/C5OB01636C
Citation: Org. Biomol. Chem., 2015,13, 9977-9983
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    Racemic total synthesis of dactyloidin and demethyldactyloidin through the DL-proline-catalyzed Knoevenagel condensation/[4 + 2] cycloaddition cascade

    H. Tan, H. Liu, X. Chen, H. Chen and S. Qiu, Org. Biomol. Chem., 2015, 13, 9977
    DOI: 10.1039/C5OB01636C

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