Issue 21, 2022
From the journal:

Organic Chemistry Frontiers

Gold-catalyzed alkyne-diol bicycloketalization enables enantioselective divergent total syntheses of attenols†

Ji Soo Shin,a   Jaeyeon Lee,a   Sunkyu Han ORCID logo *a  and  Hee-Yoon Lee ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea
E-mail: sunkyu.han@kaist.ac.kr, leehy@kaist.ac.kr

Abstract

Gold-catalyzed bicycloketalization of alkyne-diols provides synthetic advantages when compared to that of keto-diols under acidic conditions. The relative inertness of the alkyne moiety compared to that of the ketone group provided us with strategic flexibility that enabled orthogonal protecting group manipulation of five hydroxyl groups during the total syntheses of attenols. Herein, we describe our newly developed divergent synthetic route to attenols A and B, isomers with distinct bicyclic ketal cores, that was enabled by gold-catalyzed ketalization. Our total synthesis of attenols A and B overcomes the issue of isomerization between these two natural products.

Graphical abstract: Gold-catalyzed alkyne-diol bicycloketalization enables enantioselective divergent total syntheses of attenols

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Article information

DOI
https://doi.org/10.1039/D2QO01262F
Article type
Research Article
Submitted
07 Aug 2022
Accepted
02 Sep 2022
First published
05 Sep 2022

Org. Chem. Front., 2022,9, 5840-5844

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Gold-catalyzed alkyne-diol bicycloketalization enables enantioselective divergent total syntheses of attenols

J. S. Shin, J. Lee, S. Han and H. Lee, Org. Chem. Front., 2022, 9, 5840 DOI: 10.1039/D2QO01262F

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