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