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Enantioselective Total Synthesis of (-)-Lansai B and (+)-Nocardioazines A and B

Wang, Haoxuan and Reisman, Sarah E. (2014) Enantioselective Total Synthesis of (-)-Lansai B and (+)-Nocardioazines A and B. Angewandte Chemie International Edition, 53 (24). pp. 6206-6210. ISSN 1433-7851. PMCID PMC4086423. https://resolver.caltech.edu/CaltechAUTHORS:20140505-085817109

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Abstract

The concise total syntheses of the bis(pyrroloindolines) (−)-lansai B and (+)- nocardioazines A and B are reported. The key pyrroloindoline building blocks are rapidly prepared by enantioselective formal [3+2] cycloaddition reactions. The macrocycle of (+)-nocardioazine A is constructed by an unusual intramolecular diketopiperazine formation.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201402571DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201402571/abstractPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4086423PubMed CentralArticle
Additional Information:© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Article first published online: 28 Apr. 2014. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, as well as Materia, Inc. and Sigma–Aldrich for kind donations of chemicals. We are grateful to Dr. David VanderVelde for assistance with NMR structure analysis, and Mr. Larry Henling for X-ray structure determination. The Bruker KAPPA APEXII X-ray diffractometer was purchased with an NSF Chemistry Research Instrumentation award to Caltech (CHE-0639094). NMR spectra were obtained on a spectrometer funded by the NIH (RR027690). S.E.R. is a fellow of the Alfred P. Sloan Foundation, a Camille Dreyfus Teacher-Scholar, and an American Cancer Society Research Scholar. Financial support from the California Institute of Technology, the NIH (NIGMS RGM097582A, and DuPont is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
NSF Chemistry Research Instrumentation AwardCHE-0639094
NIHRR027690
Alfred P. Sloan FoundationUNSPECIFIED
Camille Dreyfus Teacher-Scholar AwardUNSPECIFIED
American Cancer Society Research Scholar AwardUNSPECIFIED
CaltechUNSPECIFIED
NIHNIGMS RGM097582A
DuPontUNSPECIFIED
Subject Keywords:cycloaddition; heterocycles; macrocycles; natural products; total synthesis
Issue or Number:24
PubMed Central ID:PMC4086423
Record Number:CaltechAUTHORS:20140505-085817109
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20140505-085817109
Official Citation:Wang, H. and Reisman, S. E. (2014), Enantioselective Total Synthesis of (−)-Lansai B and (+)-Nocardioazines A and B. Angew. Chem. Int. Ed., 53: 6206–6210. doi:10.1002/anie.201402571
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:45476
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:05 May 2014 17:56
Last Modified:03 Oct 2019 06:31

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