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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 16-17
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Original Articles

Diastered and Regiochemical Control in the Functionalization of the Allylic [dbnd] of a Natural 5-(1-Alkenyl)-2-Enono-1,5-Lactone

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Pages 1935-1945 | Published online: 05 Dec 2006

References

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  • The reduction of bromohydrine 7b with n-Bu3SnH afforded an alcohol that shows a pattern of 1H NMR signals, attributable to the C-4 and C-6 hydrogens, similar to that described by Nakata et. al. [Chem. Pharm. Bull. 1987, 35, 43551 for a δ -lactone of 5,7-anti-dihydroxy-2,3-unsaturated acid, that confirms our stereochemical assignment. We thank Dr. T. Nakata for this information
  • Kahn , S. D. , Pau , C. F. , Chamberlin , A. R. and Hehre , W. J. 1987 . J. Am. Chem. Soc. , 109 : 650
  • Chamberlin , A. R. , Mulholland , R. L. Jr. , Kahn , S. D. and Hehre , W. J. 1987 . J. Am. Chem. Soc. , 109 : 672
  • If the reacting conformation is indeed C, the low diastereoselectivity observed in this reaction could be attributed to the low electron density on the oxygen of the lactone group in comparison to the oxygen atom of allylic ethers and alcohols.9
  • Roush , W. R. , Brown , R. J. and Di Mare , M. 1983 . J. Org. Chem. , 48 : 5083
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