Yadav, Jhillu S. ; Rao, Yerragorla Gopala ; Chandrakanth, Dandekar ; Ravindar, Kontham ; Subba Reddy, Basi V. (2010) Total synthesis of aculeatins A and B from L-malic acid Helvetica Chimica Acta, 93 (12). pp. 2426-2432. ISSN 0018-019X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/hlca.20...
Related URL: http://dx.doi.org/10.1002/hlca.201000084
Abstract
An efficient total synthesis of the cytotoxic spiroketal natural products aculeatin A and B is described. The synthesis of the 1,3,5-triol moiety with appropriate configuration was accomplished from the commercially available L-malic acid. The key steps in this synthesis are the Barbier allylation, LiAlH4/LiI-mediated syn-stereoselective 1,3-asymmetric reduction, and phenyliodine bis(trifluoroacetate) (=[bis(trifluoroacetoxy)iodo]benzene; PIFA) mediated oxidative spirocyclization.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons. |
| Keywords: | Aculeatins a and B; L-Malic Acid; Stereoselective Reduction; Morpholinamide; Spirocyclization; Barbier Allylation |
| ID Code: | 62930 |
| Deposited On: | 24 Sep 2011 05:02 |
| Last Modified: | 24 Sep 2011 05:02 |
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