Synthesis of the Next Lower Homologues of Carboxylic Acids. A Convenient Route to the Queen Substance and to 9-Oxodecanoic Acid, A Prostaglandin Intermediate

References

• Black , H. K. and Weedon , B. C. L. 1953 . J. Chem. Soc. , : 1785
   Web of Science ®Google Scholar
• Ranganathan , S. , Ranganathan , D. and Mehrotra , M. M. 1978 . Tetrahedron Lett. , : 1851
   Google Scholar
• Seher , A. 1956 . Fette Seifen , 58 : 1077
   Google Scholar
• Konen , D. A. , Silbert , L. S. and Pfeffer , P. E. 1975 . J. Org. Chem. , 40 : 3253
   Web of Science ®Google Scholar
• For large scale preparations, it is advantageous to preform the Li carboxylate with LiH
   Google Scholar
• All products were identified by comparison with authentic samples and/or their spectral and physical characteristics
   Google Scholar
• Oxidation with lead tetraacetate in acetic acid
   Google Scholar
• Pfeffer , P. E. and Silbert , L. S. 1971 . J. Org. Chem. , 36 : 3290
   Google Scholar
• Sharpless , K. B. , Lauer , R. F. and Teranishi , A. Y. 1973 . J. Am. Chem. Soc. , 95 : 6137
   Web of Science ®Google Scholar
• Tsuji , J. , Masaoka , K. and Takahashi , T. 1977 . Tetrahedron Lett. , : 2267
   Google Scholar
• To avoid solubility problems it is advisable to use MeLi/Et2O instead of n-BuLi/hexane for the generation of LDA
   Google Scholar
• Eliasson , B. , Odham , G. and Petterson , B. 1971 . Acta Chem. Scand. , 25 : 2217
   Google Scholar
• Subramaniam , C. S. , Thomas , P. J. , Mamdapur , V. R. and Chadha , M. S. 1978 . Synthesis , : 468
   Google Scholar