Tandem Transacylation/Debenzylation of β-Lactones Mediated by FeCl3 Leading to γ- and δ-Lactones: Application to the Synthesis of (-)-Grandinolide

Synlett

Volumn 1996, Issue 3, 1996, Pages 278-280

  Zemribo, Ronald ^a   Champ, M S ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002545339     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5391     Document Type: Article

References (29)

1. Pommier, A.; Pons, J.-M. Synthesis 1995, 729-744. Löwe, C.; Vederas, J. Organic Prep. & Proc. Intl. 1995, 27, 305-346.
2. Pommier, A.; Pons, J.-M. Synthesis 1995, 729-744. Löwe, C.; Vederas, J. Organic Prep. & Proc. Intl. 1995, 27, 305-346.
3. For a recent application to lanthionine synthesis, see: Shao, H.; Wang, S. H. H.; Lee, C.-W.; Osapay, G.; Goodman, M. J. Org. Chem. 1995, 60, 2956-2957. Palomo, C.; Miranda, J. I.; Cuevas, C.; Odriozola, J. M. J. Chem. Soc., Chem. Commun. 1995, 1735-1736 and references cited. For a review of β-lactones, see: Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449.
4. For a recent application to lanthionine synthesis, see: Shao, H.; Wang, S. H. H.; Lee, C.-W.; Osapay, G.; Goodman, M. J. Org. Chem. 1995, 60, 2956-2957. Palomo, C.; Miranda, J. I.; Cuevas, C.; Odriozola, J. M. J. Chem. Soc., Chem. Commun. 1995, 1735-1736 and references cited. For a review of β-lactones, see: Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449.
5. For a recent application to lanthionine synthesis, see: Shao, H.; Wang, S. H. H.; Lee, C.-W.; Osapay, G.; Goodman, M. J. Org. Chem. 1995, 60, 2956-2957. Palomo, C.; Miranda, J. I.; Cuevas, C.; Odriozola, J. M. J. Chem. Soc., Chem. Commun. 1995, 1735-1736 and references cited. For a review of β-lactones, see: Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449.
6. Stevens, M. P. Polymer Chemistry; 2nd ed.; Oxford Press: New York, 1990, pp 403-407. Capozzi, G.; Roelens, S.; Talami, S. J. Org. Chem. 1993, 58, 7932-7936 and references cited.
7. Stevens, M. P. Polymer Chemistry; 2nd ed.; Oxford Press: New York, 1990, pp 403-407. Capozzi, G.; Roelens, S.; Talami, S. J. Org. Chem. 1993, 58, 7932-7936 and references cited.
8. Zemribo, R.; Romo, D. Tetrahedron Lett. 1995, 36, 4159-4162.
9. In contrast, related Mukaiyama aldols employing α-unsubstituted ketene acetals suffer from low diastereoselectivity. The t-butyldimethylsilyl ketene acetal ii was employed in a Mukaiyama aldol reaction with the same benzyloxy substituted aldehyde i under similar reaction conditions. This gave the aldol product iii in 60% de. In contrast, [2+2] cycloaddition with the same substrate gave β-lactone 1 in 96% de. (Equation Presented)
10. Canan Koch, S. S. ; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737 and references cited. Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. For example, γ-butyrolactone (+)-4 is a constituent of 30-methyloscillatoxin D: Entzeroth, M; Blackman, A. J.; Mynderse, J. S.; Moore, R. E. J. Org. Chem. 1985, 50, 1255-1259. δ-Lactones as compactin and mevinolin analogs, see: Solladie, G.; Bauder, C.; Rossi, L. J. Org. Chem. 1995, 60, 7774-7777.
11. Canan Koch, S. S. ; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737 and references cited. Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. For example, γ-butyrolactone (+)-4 is a constituent of 30-methyloscillatoxin D: Entzeroth, M; Blackman, A. J.; Mynderse, J. S.; Moore, R. E. J. Org. Chem. 1985, 50, 1255-1259. δ-Lactones as compactin and mevinolin analogs, see: Solladie, G.; Bauder, C.; Rossi, L. J. Org. Chem. 1995, 60, 7774-7777.
12. Canan Koch, S. S. ; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737 and references cited. Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. For example, γ-butyrolactone (+)-4 is a constituent of 30-methyloscillatoxin D: Entzeroth, M; Blackman, A. J.; Mynderse, J. S.; Moore, R. E. J. Org. Chem. 1985, 50, 1255-1259. δ-Lactones as compactin and mevinolin analogs, see: Solladie, G.; Bauder, C.; Rossi, L. J. Org. Chem. 1995, 60, 7774-7777.
13. Canan Koch, S. S. ; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737 and references cited. Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. For example, γ-butyrolactone (+)-4 is a constituent of 30-methyloscillatoxin D: Entzeroth, M; Blackman, A. J.; Mynderse, J. S.; Moore, R. E. J. Org. Chem. 1985, 50, 1255-1259. δ-Lactones as compactin and mevinolin analogs, see: Solladie, G.; Bauder, C.; Rossi, L. J. Org. Chem. 1995, 60, 7774-7777.
14. Vieira, P. C.; Yoshida, M.; Gottlieb, O. R.; Filho, H. F. P.; Nagem, T. J.; Filho, R. B. Phytochem. 1983, 22, 711-713.
15. Ganem, B.; Small, V. R., Jr. J. Org. Chem. 1974, 39, 3728-3730.
16. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532-5534.
17. Seebach, D.; Chow, H.-F.; Jackson, R. F. W.; Lawson, K.; Sutter, M. A.; Thasrivongs, S.; Zimmermann, J. Liebigs Ann. Chem. 1986, 1281-1308.
18. Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc. Perkin Trans. 1991, 133-137.
19. A representative procedure as described for γ-lactone 4 follows: β-Lactone 2 (210 mg; 1.02 mmol) was dissolved in 30 mL of methylene chloride. Ferric chloride (31 mg; 0.2 mmol) was added to the stirred solution of β-lactone at ambient temperature. The black slurry was stirred at the same temperature for 42 hours. The reaction mixture was then passed through a short florisil column with ethyl acetate as eluent. Concentration under reduced pressure gave a yellow oil. Purification of the crude material by flash column chromatography (gradient elution: 20% EtOAc / hexane → EtOAc) gave 86 mg (74%) of γ-butyrolactone 4 as a colorless oil along with 19 mg (9%) of the benzylated γ-butyrolactone 11. The spectral characteristics of γ-butyrolactone 4 correlated with that reported in the literature (ref. 6).
20. All new compounds gave spectral data consistent with their assigned structure.
21. Although it appears that a single diastereomer of the bromide 14 is formed, the configuration has not been determined.
22. Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J.Am. Chem. Soc. 1985, 107, 7105-7109.
23. Mulzer, J.; Bruntrup, G. Agnew. Chem. Int. Ed. Engl. 1979, 18, 793-794. Mulzer, J.; Pointner, A.; Straber, R.; Hoyer, K.; Nagel, U. Tetrahedron Lett. 1995, 36, 3679-3682. Black, T. H.; McDermott, T. S. Syn. Commun. 1990, 20, 2959-2964 and references cited.
24. Mulzer, J.; Bruntrup, G. Agnew. Chem. Int. Ed. Engl. 1979, 18, 793-794. Mulzer, J.; Pointner, A.; Straber, R.; Hoyer, K.; Nagel, U. Tetrahedron Lett. 1995, 36, 3679-3682. Black, T. H.; McDermott, T. S. Syn. Commun. 1990, 20, 2959-2964 and references cited.
25. Mulzer, J.; Bruntrup, G. Agnew. Chem. Int. Ed. Engl. 1979, 18, 793-794. Mulzer, J.; Pointner, A.; Straber, R.; Hoyer, K.; Nagel, U. Tetrahedron Lett. 1995, 36, 3679-3682. Black, T. H.; McDermott, T. S. Syn. Commun. 1990, 20, 2959-2964 and references cited.
26. Baldwin, J. E. J. Chem. Soc. Chem. Commun. 1976, 734-736.
27. 2O, 91% (viii) NaI, acetone, reflux, 73%.
28. 3 (M+H): 459.3838, found: 459.3867. The melting point discrepancy may be due to contamination of natural (-)-grandinolide with lactones differing only in the length of the side chain which were also found to be present in extracts (ref. 7). Prof. Gottlieb no longer had a sample of (-)-grandinolide for direct spectral comparison.
29. Mead, K. T.; Yang, H.-L. J. Org. Chem. 1990, 55, 2991-2992 and references cited.