An Enantioselective Epoxide Rearrangement - Claisen Rearrangement Approach to Prostaglandins and (+)-Iridomyrmecin

Synlett

Volumn 1997, Issue 6, 1997, Pages 657-658

  Hodgson, David M ^a   Gibbs, Andrew R ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002835625     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3253     Document Type: Article

References (18)

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2. Review: Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron, 1996, 46, 14361-14384.
3. The individual diols (-)-2 and (+)-2 are commercially available from Oxford Asymmetry Ltd. The precursor epoxide 1 can be prepared in four steps from diethyl diallylmalonate (ref. 1 and Nugent, W. A.; Feldman, J.; Calabrese, J. C. J. Am. Chem. Soc. 1995, 117, 8992-8998). For another potential enantioselective approach see: Tomooka, K.; Ishikawa, K.; Al-Masum, M.; Nakai, T. Synlett 1993, 645-646.
4. The individual diols (-)-2 and (+)-2 are commercially available from Oxford Asymmetry Ltd. The precursor epoxide 1 can be prepared in four steps from diethyl diallylmalonate (ref. 1 and Nugent, W. A.; Feldman, J.; Calabrese, J. C. J. Am. Chem. Soc. 1995, 117, 8992-8998). For another potential enantioselective approach see: Tomooka, K.; Ishikawa, K.; Al-Masum, M.; Nakai, T. Synlett 1993, 645-646.
5. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York; 1989; pp. 249-309.
6. Fukuzawa, A.; Sato, H.; Masamune, T. Tetrahedron Lett. 1987, 28, 4303-4306.
7. 13C NMR and microanalysis and/or high resolution mass spectrometry.
8. Hughes, D. L. Org. React. 1992, 42, 335-656.
9. Raucher, S.; Schindele, D. C. Synth. Commun. 1987, 17, 637-646.
10. Begley, M. J.; Madeley, J. P.; Pattenden, G.; Smith, G. F. J. Chem. Soc., Perkin Trans, 1 1992, 57-65.
11. +, 72%], 248 (13), 247 (100), 246 (4), 229 (15), 204 (14) and 187 (28).
12. Corey, E. J.; Grieco, P. A. Tetrahedron Lett. 1972, 107-109.
13. Corey, E. J.; Loh, T-P. J. Am. Chem. Soc., 1991, 113, 8966-8967.
14. Grieco, P. A.; Srinivasan, C. V. J. Org. Chem. 1981, 46, 2591-2593.
15. 2S was prepared according to: Wuts. P. G. M. Synth. Commun. 1981, 11, 139-140.
16. 2S was prepared according to: Wuts. P. G. M. Synth. Commun. 1981, 11, 139-140.
17. Cavill, G. W. K.; Ford, D. L.; Locksley, H. D. Aust. J. Chem. 1956, 9, 288-293.
18. Lee, E.; Yoon, C. H. J. Chem. Soc., Chem. Commun. 1994, 479-481, and references cited therein.