Issue 39, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
06 Aug 2015
Accepted
13 Aug 2015
First published
13 Aug 2015

Org. Biomol. Chem., 2015,13, 9977-9983

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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