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Issue 8, 2017
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Total synthesis of (+)-herboxidiene/GEX 1A

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Abstract

A total synthesis of (+)-herboxidiene/GEX 1A has been accomplished from (R)- and (S)-lactate esters in a highly efficient manner. Key steps of the synthesis involve substrate-controlled titanium-mediated aldol reactions from chiral lactate-derived ethyl ketones, an oxa-Michael cyclization, an Ireland–Claisen rearrangement, and a Suzuki coupling. Furthermore, computational studies of the oxa-Michael reaction have unveiled the dramatic influence of intramolecular hydrogen bonds on the stereochemical outcome of such cyclizations, whereas biological analyses have clearly proved the important cytoxicity of (+)-herboxidiene/GEX 1A.

Graphical abstract: Total synthesis of (+)-herboxidiene/GEX 1A

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Supplementary files

Article information


Submitted
12 Jan 2017
Accepted
30 Jan 2017
First published
30 Jan 2017

Org. Biomol. Chem., 2017,15, 1842-1862
Article type
Paper

Total synthesis of (+)-herboxidiene/GEX 1A

A. Gómez-Palomino, M. Pellicena, K. Krämer, P. Romea, F. Urpí, G. Aullón and J. M. Padrón, Org. Biomol. Chem., 2017, 15, 1842
DOI: 10.1039/C7OB00072C

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