Short total syntheses of both the putative and actual structures of the clerodane diterpenoid (+/-)-sacacarin by double annulation.
| Author | |
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| Abstract | :
[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 | :
2001
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| Journal | :
Organic letters
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| Volume | :
3
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| Issue | :
25
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| Number of Pages | :
4027-30
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| Date Published | :
2001
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| ISSN Number | :
1523-7060
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| URL | :
https://dx.doi.org/10.1021/ol016748j
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| DOI | :
10.1021/ol016748j
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| Short Title | :
Org Lett
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