Total synthesis of biselide A
Open Access
- 12 March 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 12 (15), 5534-5543
- https://doi.org/10.1039/d0sc06223e
Abstract
A total synthesis of the marine macrolide biselide A is described that relies on an enantiomerically enriched α-chloroaldehyde as the sole chiral building block. Several strategies to construct the macrocycle are presented including a macrocyclic Reformatsky reaction that ultimately provides access to the natural product in a longest linear sequence of 18 steps. Biological testing of synthetic biselide A suggests this macrolide disrupts cell division through a mechanism related to the regulation of microtubule cytoskeleton organization. Overall, this concise synthesis and insight gained into the mechanism of action should inspire medicinal chemistry efforts directed at structurally related anticancer marine macrolides.Funding Information
- Natural Sciences and Engineering Research Council of Canada
- Michael Smith Foundation for Health Research
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