Short total syntheses of both the putative and actual structures of the clerodane diterpenoid (+/-)-sacacarin by double annulation.
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Abstract |
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[reaction: see text] The putative structure of the naturally occurring clerodane diterpenoid (+/-)-sacacarin has been prepared in only 10 steps, six of which are C-C bond-forming steps, in a chemo-, regio-, and diastereoselective manner. The key part of the synthesis is the double annulation (double Michael, Pinner, and Dieckmann reaction) of a tethered carbon diacid and 3-butyn-2-one. A corrected structure for sacacarin is proposed, and the structure is proven by synthesis. |
Year of Publication |
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2001
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Journal |
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Organic letters
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Volume |
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3
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Issue |
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25
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Number of Pages |
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4027-30
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Date Published |
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2001
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ISSN Number |
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1523-7060
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URL |
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https://dx.doi.org/10.1021/ol016748j
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DOI |
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10.1021/ol016748j
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Short Title |
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Org Lett
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