Total Synthesis of Cryptocaryol A by Enantioselective Iridium-Catalyzed Alcohol C-H Allylation

Felix Perez; Andrew R Waldeck; Michael J Krische

doi:10.1002/anie.201600591

Total Synthesis of Cryptocaryol A by Enantioselective Iridium-Catalyzed Alcohol C-H Allylation

Angew Chem Int Ed Engl. 2016 Apr 11;55(16):5049-52. doi: 10.1002/anie.201600591. Epub 2016 Mar 11.

Authors

Felix Perez¹, Andrew R Waldeck¹, Michael J Krische²

Affiliations

¹ University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA.
² University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA. mkrische@mail.utexas.edu.

Abstract

The polyketide natural product cryptocaryol A is prepared in 8 steps via iridium catalyzed enantioselective diol double C-H allylation, which directly generates an acetate-based triketide stereodiad. In 4 previously reported total syntheses, 17-28 steps were required.

Keywords: enantioselective synthesis; iridium; polyketide; total synthesis; transfer hydrogenation.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Allyl Compounds / chemistry*
Catalysis
Iridium / chemistry*
Pyrones / chemical synthesis*
Stereoisomerism

Substances

Alcohols
Allyl Compounds
Pyrones
cryptocaryol A
Iridium

Abstract

Publication types

MeSH terms

Substances

Grants and funding