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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 11
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Original Articles

Stereoselective Synthesis of (5R, 65)-(-) Erythro-6-Acetoxy-5-Dodecanolide, A Lower Homologue of a Mosquito Oviposition Attractant Pheromone, from Argentilactone

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Pages 1287-1297 | Published online: 05 Dec 2006

References

  • Priestap , H. A. , Bonafede , J. D. and Rúveda , E. A. 1977 . Phytochemistry , 16 : 1579
  • Olivieri , A. C. , Gonzalez-Sierra , M. and Rúveda , E. . 1986 . J. Org. Chem. , 51 : 2824
  • Laurence , B. R. and Pickett , J. A. 1982 . J. Chem. Soc. Chem. Commun , : 59
  • Guo-qiang , L. , Hai-jian , X. , Bi-chi , W. , Guong-zhong , G. and Wei-shan , Z. 1985 . Tetrahedron Lett. , : 1233 See however ref 2 of, in which it is mentioned that Professor K. Mori, (Tokyo University) informed to one of the chinese authors that the natural pheromone was shown to be 5R, 65
  • Machiya , K. , Ichimoto , I. , Kirihata , M. and Ueda , H. 1985 . Agric. Biol. Chem , 49 : 643
  • Fugariti , C. , Grasselli , P. and Servi , S. 1982 . J. Chem. Soc. Chem. Commun. , : 1285 For other total synthesis of 6-acetoxy-5-hexadecanolide see: K. Nori, T. Otsuka, Tetrahedron 39, 3267 (1983); T. Sato, M. Watanabe, N. Honda, T. Fujisawa, Chem. Lett., 1775 (1934); N. Ochiai, T. Ukita, Y. Nagao, E. Fujita, J. Chem. Soc. Chem. Commun., 637 (1985)
  • Dais , P. and Perlin , A. S. 1985 . Can. J. Chem. , 63 : 1009 For the determination of the configuration and conformation of the epoxypropyl side-chain of a lactone related to 1, by spin-lattice relaxation rates and nuclear Overhauser enhancement experiments, see, see also R. M. Rabanal, J. Escudero, M. Martin-Lomas, S. Valverde, A. Perales and J. Fayos, Carbohydr. Res. 141, 49 (1985). 8. C.H. Behrens, K.B. Sharpless, J. Org. Chem, 50, 5696 (1985) and references cited therein
  • Behrens , C. H. and Sharpless , K. B. 1985 . J. Org. Chem , 50 : 5696 and references cited therein
  • Work is in progress to determine the biological activity of 2a.
  • Mori , K. In spite of the data reported by (reference 6), for 2b and the corresponding threo diastereoisomer, we have found, in agreement with K. Machiya et. al;, (reference 5), that the 1H NMR data of the erythro and threo isomers 2a and 2g are practically identical

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