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Published April 7, 2017 | Published + Supplemental Material
Journal Article Open

Enantioselective Synthesis of (−)-Acetylapoaranotin


The first enantioselective total synthesis of the epipolythiodiketopiperazine (ETP) natural product (−)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (−)-emethallicin E and (−)-haemotocin are also achieved through the preparation of a symmetric cyclohexadienol-containing diketopiperazine.

Additional Information

© 2017 American Chemical Society. ACS Editors' Choice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Received: February 17, 2017; Published: March 28, 2017. We gratefully acknowledge Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, and Dr. David VanderVelde for assistance with NMR structure analysis. We thank Materia, Inc. and Sigma-Aldrich for donations of chemicals. We also thank Amy McCarthy, Geanna Min, and Madeleine Kieffer of Caltech for the preparation of synthetic intermediates. Fellowship support was provided by the Department of Defense (DoD) through the National Defense Science & Engineering Graduate Fellowship Program (J.A.C.), the NSF Graduate Research Fellowship Program (J.A.C., Grant No. DGE-0703267), and the Swiss National Science Foundation (P.R.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute investigator. Financial support from the NIH (NIGMS RGM097582A), the American Cancer Society, the Research Corporation Cottrell Scholar program, and DuPont is gratefully acknowledged.

Attached Files

Published - acs.orglett.7b00418.pdf

Supplemental Material - ol7b00418_si_001.pdf


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