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Efficient Asymmetric Synthesis of abeo-Abietane-Type Diterpenoids by Using the Intramolecular Heck Reaction

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Department of Pharmaceutical Manufacturing Chemistry, 21st COE Program, Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan
[email protected]
Cite this: J. Org. Chem. 2010, 75, 1, 190–196
Publication Date (Web):December 7, 2009
https://doi.org/10.1021/jo901972b
Copyright © 2009 American Chemical Society
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    Abstract

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    The synthesis of the abeo-abietane-type diterpenoids, i.e., (−)-dichroanal B, (−)-dichroanone, and taiwaniaquinone H, was achieved by using the intramolecular asymmetric Heck reaction. Our synthetic routes required fewer steps and gave a much higher overall yield and ee within shorter steps than those for racemic and antipodal forms reported to date (10, 12, and 13 steps with an overall yield of 50%, 40%, and 39%, and 94%, 98%, and 98% ee, respectively).

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    1H NMR and 13C NMR spectra for all new compounds, an ORTEP for 19, and complete experimental details following the general procedures. This material is available free of charge via the Internet at http://pubs.acs.org.

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