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Enantioselective Synthesis of (−)-Acetylapoaranotin

Wang, Haoxuan and Regan, Clinton J. and Codelli, Julian A. and Romanato, Paola and Puchlopek-Dermenci, Angela L. A. and Reisman, Sarah E. (2017) Enantioselective Synthesis of (−)-Acetylapoaranotin. Organic Letters, 19 (7). pp. 1698-1701. ISSN 1523-7060. PMCID PMC5387676. https://resolver.caltech.edu/CaltechAUTHORS:20170329-093225716

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/acs.orglett.7b00418DOIArticle
http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b00418PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b00418PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5387676/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
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.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
NSF Graduate Research FellowshipDGE-0703267
Swiss National Science Foundation (SNSF)UNSPECIFIED
American Cancer SocietyUNSPECIFIED
Heritage Medical Research InstituteUNSPECIFIED
NIHRGM097582A
Cottrell Scholar of Research CorporationUNSPECIFIED
DuPontUNSPECIFIED
Issue or Number:7
PubMed Central ID:PMC5387676
Record Number:CaltechAUTHORS:20170329-093225716
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170329-093225716
Official Citation:Enantioselective Synthesis of (−)-Acetylapoaranotin Haoxuan Wang, Clinton J. Regan, Julian A. Codelli, Paola Romanato, Angela L. A. Puchlopek-Dermenci, and Sarah E. Reisman Organic Letters 2017 19 (7), 1698-1701 DOI: 10.1021/acs.orglett.7b00418
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75505
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:29 Mar 2017 16:41
Last Modified:03 Oct 2019 16:51

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