A Thero and Cram Selective Aldol-Lactonization Reaction and Its Application to the Synthesis of Prelog Djerassi Lactonic Acid

Journal of the American Chemical Society

Volumn 104, Issue 1, 1982, Pages 357-358

  Schlessinger, R H ^a   Poss, M A ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748671692     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00365a094     Document Type: Article

References (31)

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3. Lactone 1 has been isolated as a degradation product of neomethymycin by: Djerassi, C.; Halpern, O. J. J. Am. Chem. Soc. 1957, 79, 2022, 3926; In addition, 1 has been obtained from picromycin by:
4. Anliker, R.; Gubler, K. Helv. Chim. Acta 1957, 40, 119.
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6. The detailed stereochemical features of 1 were determined by: Rickards, R. W.; Smith, R. M. Tetrahedron Lett. 1970, 1025.
7. Syntheses of racemic 1 have been reported by (a) Masamune, S.; Kim, C. U.; Wilson, K. E.; Spessard, G. O.; Georghiou, P. E.; Bates, G. S. J. Am. Chem. Soc. 1975, 97, 3512.
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14. Syntheses of 1 from acyclic precursors have been reported by: (a) Hirama, M.; Garvey, D. S.; Lu, L.D.-L.; Masamune, S. Tetrahedron Lett. 1981, 22, 2533 1979, 3937.
15. Bartlett, P. A.; Adams, J. L. J. Am. Chem. Soc. 1980, 102, 337.
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25. Aldehyde 6 was obtained from its corresponding ester by LAH reduction followed by PCC oxidation. A preparation of the racemic ester is described by: Cohen, N.; Eichel, W. F.; Lopresti, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505.
26. The aldehyde 7 was obtained from its corresponding racemic alcohol by PCC oxidation. The preparation of this alcohol is described by: Corey, E. J.; Bock, M. G. Tetrahedron Lett. 1975, 2643.
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