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Synlett 2009(18): 2949-2952  
DOI: 10.1055/s-0029-1218003
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Concise Asymmetric Total Synthesis of ent-Guadinomic Acid from an Epoxy Alkenol

Hyemi Kim, Myung-Yeol Kim, Jinsung Tae*
Department of Chemistry and Center for Bioactive Molecular Hybrids (CBMH), Yonsei University, Seoul 120-749, Korea
Fax: +82(2)3647050; e-Mail: jstae@yonsei.ac.kr;
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Publication History

Received 29 July 2009
Publication Date:
02 October 2009 (online)

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Concise Asymmetric Total Synthesis of ent-Guadinomic Acid from an Epoxy AlkenolSynlett 2009; 2009(18): e4-e4
DOI: 10.1055/s-0029-1218348

Abstract

A highly efficient asymmetric total synthesis of ent-guadinomic acid [(-)-K01-0509 B] was accomplished from the known epoxy alkenol which is resolved by HKR method. Cross metathesis of the alkene part with acrylate and epoxide opening with azide followed by intramolecular guanidine formation reactions furnished ent-guadinomic acid.

Key words

cyclic guanidine - epoxides - guadinomic acid - meta­thesis - total synthesis

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15

The reason for the improvement of the regioselectivity is not clear.

17

The bulky and less nucleophilic Hünig’s base might minimize side reactions associated with the highly reactive Tf2O.