Binreduction of (R)-carvone and regioselective baeyer-villiger oxidations: Application to the asymmetric synthesis of cryptophycin fragment A

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8405-8408

  Varie, David L ^a   Brennan, John ^a   Briggs, Barbara ^a   Cronin, Jason S ^a   Hay, David A ^a   Rieck III, John A ^a   Zmijewski, Milton J ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARVONE; CRYPTOPHYCIN DERIVATIVE; CRYPTOPHYCIN FRAGMENT A; CYCLOHEXANONE; DEPSIPEPTIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

DRUG SYNTHESIS; ENANTIOMER; OXIDATION; REDUCTION; REVIEW; STEREOCHEMISTRY;

EID: 0032512006     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01784-5     Document Type: Article

References (26)

1. 1. Schwartz, R. E.; Hirsch, C. F.; Sesin, D. F.; Flor, J. E.; Chartrain, M.; Fromtling, R. E.; Harris, G. H.; Salvatore, M. J.; Liesch, J. M.; Yudin, K.J. J. Ind. Microbiol. 1990, 5, 113.
2. 2. a) Trimurtulu, G.; Ohtani, I.; Patterson, G. M.; Moore, R. E.; Corbett, T. H.; Valeriote, F. A.; Demchik, L. J. Am. Chem. Soc. 1994, 116, 4729.
3. b) Golakoti, T.; Ogino, J.; Heltzel, C. E.; Husebo, T. Le; Jensen, C. M.; Larsen, L. K.; Patterson, G. M. L.; Moore, R. E.; Mooberry, S. L.; Corbet, T. H.; Valeriote, F. A. J. Am. Chem. Soc. 1995, 117, 12030.
4. 3. Barrow, R. A.; Hemscheidt, T.; Liang, J.; Paik, S.; Moore, R. E.; Tius, M. A. J. Am. Chem. Soc. 1995, 117, 2479.
5. 4. a) Shimizu, I.; Furuyama, M. Tetrahedron: Asymm. 1998, 9, 1351.
6. b) de Muss, J-M.; Erg, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavallee, J-F. Bioorg. Med. Chem. Lett. 1996, 6, 1111.
7. c) Rej, R.; Nguygen, D.; Go, B. Fortin, S.; Lavallee, J-F. J. Org. Chem. 1996, 61, 6289.
8. d) Salamonczyck, G. M.; Han, K.; Guo, Z-W.; Sih, C. J. J. Org. Chem. 1996, 61, 6893.
9. e) Ali, S. M.; Goerg, G. I. Tetrahedron Lett. 1997, 38, 1703.
10. f) Leahy, J. W.; Gardinier, K. M. J. Org. Chem. 1997, 62, 7098.
11. 5. a) Chen, X.; Sichang, S.; Li, T.; Li, Y. Synthesis 1992, 1061.
12. b) For a report of a stereoselective reduction of carvone to trans-dihydrocarvone with NaHTe see: Yamashita, M.; Tanaka, Y; Akishi, A.; Nishida, M. J. Org. Chem. 1994, 59, 3500.
13. 6. This mixture of cis and trans-4 is commercially available from Glidco Organics Corp., Jacksonville, FL.
14. 7. Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159.
15. 8. Previous bioreductions of (R)-carvone to neodihydrocarveol (5): a) Noma, Y.; Nonomura, S. Agr. Biol. Chem. 1974, 38, 741.
16. b) Hirata, T.; Hamada, H.; Aoki, T.; Suga, T. Phytochemistry 1982, 21, 2209.
17. 9. In the presence of Trigonopsis variablis, trans-4 was independently reduced to 5 with 99% de; cis-4 was reduced under similar conditions to give a 1:1 mixture of the two possible dihydrocarveol diastereomers.
18. 10. a) Swarts, H. J; Verstegen-Hacksma, A. A.; Jansen, B. J. M.; deGroot, A. Tetrahedron 1994, 50, 10083.
19. b) Schreiber, S. L.; Liew, W.-F. Tetrahedron Lett. 1983, 24, 2363.
20. 11. Anelli, P.; Montanari, F.; Quici, S. Organic Syntheses 1990, 69, 212 and references therein.
21. 12. For a review of the Bayer-Villiger oxidation see: Krow, G. R. Organic Reactions 1993, 43, 251.
22. 13. Compounds 2a-c and 9a-c were separated by chromatography and distinguished by 500 MHz proton NMR decoupling and HETCOR experiments. Regioisomer ratios in the crude lactone mixtures were determined by integration of the methine proton signals α to the oxygen.
23. 14. Cooper M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett. 1990, 533.
24. 15. Siddall, J.B.; Fung, S. J. Am. Chem. Soc. 1980, 102, 6580.
25. 3H cannot be fully explained by simple protonation of the β-oxygen. A more detailed study of this reaction will be reported separately.
26. 17. The intermediate mesylate was not observed in any of the reactions. When methanesulfonyl chloride was used, in additon to a 4:1 mixture of 1a:14, a 25% yield of the benzylic chloride was isolated. The chloride did not eliminate under the reaction conditions.