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Short total syntheses of both the putative and actual structures of the clerodane diterpenoid (+/-)-sacacarin by double annulation.

Author
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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