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Total Synthesis of (+)-Galbulimima Alkaloid 13 and (+)-Himgaline

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Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138
Cite this: J. Am. Chem. Soc. 2007, 129, 5, 1048–1049
Publication Date (Web):January 17, 2007
https://doi.org/10.1021/ja0684996
Copyright © 2007 American Chemical Society

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    Abstract

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    The stereoselective syntheses of (+)-himgaline (1) and (+)-GB13 (2) are described. Important diastereoselective bond constructions include an intramolecular Diels−Alder reaction, an intramolecular Michael addition, and an intramolecular enamine aldol addition.

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    Experimental procedures, spectroscopic data, and copies of 1H and 13C NMR spectra for all compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    30. K.-i. Tadano. 2.17 Selected Diastereoselective Reactions: Intramolecular Diels–Alder Reactions. 2012, 504-524. https://doi.org/10.1016/B978-0-08-095167-6.00210-X
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    39. . Six‐Membered Carbocycles. 2010, 197-422. https://doi.org/10.1002/9780470872215.ch4
    40. Weiwei Zi, Shouyun Yu, Dawei Ma. A Convergent Route to the Galbulimima Alkaloids (−)‐GB 13 and (+)‐GB 16. Angewandte Chemie 2010, 122 (34) , 6023-6026. https://doi.org/10.1002/ange.201002299
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    47. Darrin W. Hopper, Kristina M.K. Kutterer, Aimee L. Crombie, Jeremy J. Clemens. Chapter 6.1: Six-membered ring systems: pyridine and benzo derivatives. 2009, 289-332. https://doi.org/10.1016/S0959-6380(09)70016-9

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