Stereoselective formal total synthesis of (+)-methynolide

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5882-5885

  Yadav, J S ^a   Pratap, T V ^a   Rajender, V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDATION; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

DESYMMETRIZATION; METHYNOLIDES; NOZAKI-HIYAMA-KISHI REACTION;

ORGANIC COMPOUNDS;

ALLYL ALCOHOL; CARBON; METHYNOLIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; NOZAKI HIYAMA KISHI REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 34547135676     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0704762     Document Type: Article

References (47)

1. (a) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585-607.
2. (b) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569-3624.
3. (c) Boeckman, R. H.; Goldstein, M. In The Total Synthesis of Natural Products; Apsimon, J., Ed.; Wiley: New York, 1988; Vol. 7, p 1.
4. (d) Tatsuda, K. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer: Berlin, 1990; p 1.
5. Djerassi, C.; Halpern, O. Tetrahedron 1958, 3, 255-268.
6. Kinumaki, A.; Suzuki, M. J. Chem. Soc., Chem. Commun. 1972, 744-745.
7. (a) Masamune, S.; Kim, C. U.; Wilson, K. E.; Spessard, G. O.; Georghiou, P. E.; Bates, G. S. J. Am. Chem. Soc. 1975, 97, 3512-3513.
8. (b) Masamune, S.; Yamamoto, H.; Kamata, S.; Fukusawa, A. J. Am. Chem. Soc. 1975, 97, 3513-3515.
9. (a) Djerassi, C.; Zderic, J. A. J. Am. Chem. Soc. 1956, 78, 6390-6395.
10. (b) For a review on the synthesis of Prelog Djerassi lactone, see: Martin, S. F.; Guinn, D. E. Synthesis 1991, 245-262.
11. (a) Nakano, A.; Takimoto, S.; Inanaga, J.; Katsuki, T.; Ouchida, S.; Inoue, K; Aiga, M.; Okukado, N.; Yamaguchi, M. Chem. Lett. 1979, 1019-1020.
12. (b) Inanaga, J.; Katsuki, T.; Takimoto, S.; Ouchida, S.; Inoue, K.; Nakano, A.; Okukado, N.; Yamaguchi, M. Chem. Lett. 1979, 1021-1024.
13. (c) White, J. D.; Fukuyama, Y. J. Am. Chem. Soc. 1979, 101, 226-228
14. (d) Oikawa, Y.; Tanaka, T.; Yonemitsu, O. Tetrahedron Lett. 1986, 27, 3647-3650.
15. (e) Oikawa, Y.; Tanaka, T.; Horita, K.; Noda, I.; Nakajima, N.; Kakusawa, N.; Hamada, T.; Yonemitsu, O. Chem. Pharm. Bull. 1987, 35, 2184-2195.
16. (f) Oikawa, Y.; Tanaka, T.; Hamada, T.; Yonemitsu, O. Chem. Pharm. Bull. 1987, 35, 2196-2202.
17. (g) Tanaka, T.; Oikawa, Y.; Nakajima, N.; Hamada, T.; Yonemitsu, O. Chem. Pharm. Bull. 1987, 35, 2203-2208.
18. (h) Ditrich, K. Liebigs Ann. Chem. 1990, 789-793.
19. (a) Grieco, P. A.; Ohfune, Y.; Yokoyama, Y.; Owens, W. J. Am. Chem. Soc. 1979, 101, 4749-4752.
20. (b) Ireland, R. E.; Daub, J. P.; Mandel, G. S.; Mandel, N. S. J. Org. Chem. 1983, 48, 1312-1325.
21. (c) Vedejs, E.; Buchanan, R. A.; Watanabe, Y. J. Am. Chem. Soc. 1989, 111, 8430-8438.
22. (d) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron 2002, 58, 5909-5922.
23. (a) Yadav, J. S.; Srinivas Rao, C.; Chandrasekhar, S.; Rama Rao, A. V. Tetrahedron Lett. 1995, 36, 7717-7720.
24. (b) Yadav, J. S.; Abraham, S.; Muralidhar Reddy, M.; Sabitha, G.; Ravi Sankar, A.; Kunwar, A. C. Tetrahedron Lett. 2001, 42, 4713-4716.
25. (c) Yadav, J. S.; Ahmed, M. M. Tetrahedron Lett. 2002, 43, 7147-7150.
26. (d) Yadav, J. S.; Srinivas, R.; Sathaiah, K. Tetrahedron Lett. 2006, 47, 1603-1606.
27. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
28. Mitsunobu, O. Synthesis 1981, 1-28.
29. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
30. Evans, D. A. J. Org. Chem. 1990, 55, 5190-5192.
31. Stork, G.; Takahashi, J. J. Am. Chem. Soc. 1977, 99, 1275-1276.
32. Oikawa, Y.; Tanaka, T.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1984, 25, 5397-5400.
33. Barton, D. H. R.; Mc Combie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
34. Kloosterman, M.; Slaghek, T.; Hermans, J. P. G.; VanBoom, J. H.; Recl, J. R. Neth. Chem. Soc. 1984, 103, 335-341.
35. Schreiber, S. L.; Wang, Z.; Schulte, G. Tetrahedron Lett. 1988, 29, 4085-4088.
36. Corey, E. J.; Cho, H.; Rücker, C.; Hua, D. H. Tetrahedron Lett. 1985, 26, 5239-5242.
37. Prakash, C.; Saleh, S.; Blair, A. Tetrahedron Lett. 1989, 30, 19-22.
38. Lang, R. W.; Hansen, H. J. Helv. Chim. Acta 1980, 63, 438-455.
39. (a) Jorgenson, M. J. Tetrahedron Lett. 1962, 3, 559-562.
40. (b) Dilling, W. L.; Plepys, R. A. J. Org. Chem. 1970, 35, 2971-2976.
41. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
42. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
43. Colvin, E. W.; Robertson, A. D.; Wakharkar, S. J. Chem. Soc., Chem. Commun. 1983, 312-314.
44. Phillips, K. D.; Zemlicka, J.; Horowitz, J. P. Carbohydr. Res. 1973, 30, 281-286.
45. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769-3772.
46. Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179-3181.
47. Krauss, G. A.; Taschner, M. J. Org. Chem. 1980, 45, 1175-1176.