Conversion of a gibberellin aldehyde into a 20-norkaurenoid lactone

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8937-8940

  Benjamin, Lynda J ^a   Mander, Lewis N ^a   Willis, Anthony C ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

GIBBERELLIN DERIVATIVE; KAURENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030566870     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02052-7     Document Type: Article

References (35)

1. 1. Bearder, J.R.; MacMillan, J.; Wels, C.M.; Chaffey, M.B.; Phinney, B.O. Phytochemistry, 1974, 13, 911-917. Hedden, P.; Phinney, B.O.; MacMillan, J.; Sponsel, V.M. Phytochemistry, 1977, 16, 1913-1917. Hanson, J.R. Nat. Prod. Rep. 1991, 9, 139-151.
2. 1. Bearder, J.R.; MacMillan, J.; Wels, C.M.; Chaffey, M.B.; Phinney, B.O. Phytochemistry, 1974, 13, 911-917. Hedden, P.; Phinney, B.O.; MacMillan, J.; Sponsel, V.M. Phytochemistry, 1977, 16, 1913-1917. Hanson, J.R. Nat. Prod. Rep. 1991, 9, 139-151.
3. 1. Bearder, J.R.; MacMillan, J.; Wels, C.M.; Chaffey, M.B.; Phinney, B.O. Phytochemistry, 1974, 13, 911-917. Hedden, P.; Phinney, B.O.; MacMillan, J.; Sponsel, V.M. Phytochemistry, 1977, 16, 1913-1917. Hanson, J.R. Nat. Prod. Rep. 1991, 9, 139-151.
4. 2. Mander, L.N. Chem. Rev. 1992, 92, 573-612.
5. 3. Cross, B. E.; Norton, K.; Stewart, J.C. J. Chem. Soc. (C), 1968, 1054-1063.
6. 4. Hedden, P.; MacMillan, J.; Phinney, B.O. J. Chem. Soc. Perkin Trans. I, 1974, 587-592.
7. 5. Cross, B.E.; Gatfield, I.L. J. Chem. Soc. (C), 1971, 1539-1541.
8. 6. Somei, M.; Okamoto, T. Chem. Pharm. Bull. (Japan), 1970, 18, 2135-2140.
9. 7. Fujita, E.; Shibuya, M.; Nakamura, D.; Okada, Y.; Fujita, T. J. Chem. Soc. Perkin Trans. I, 1974, 165-177.
10. 8. Fujita, E.; Node, M. Progress in the Chemistry of Organic Natural Products, 1984, 46, 77-157.
11. 9. Fujita, E.; Fujita, T.; Katayama, H.; Shibuya, M.; Shingu, T. J. Chem. Soc. (C), 1970, 1674-1681.
12. 10. Kubo, I.; Pettei, M.J.; Hirotsu, K.; Tsuji, H.; Kubota, T. J. Am. Chem. Soc. 1978, 100, 628-630
13. 11. Fujita, E.; Fujita, T.; H.; Shibuya, M. J. Chem. Soc. Chem. Commun. 1966, 297.
14. 12. Cf. Corey, E.J.; Ohno, M.; Mitra R.B.; Vatakencherry, P.A. J. Am. Chem. Soc. 1964, 86, 478-485.
15. 13C-NMR spectra, mass spectra, high resolution mass measurements and/or satisfactory microanalyses.
16. 14. Cf. Lischewski, M.; Adam, G. Tetrahedron Lett. 1980, 21, 1627-1628.
17. 15. Grieco, P.A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485-1486.
18. 16. VanRheenan, V.; Kelly, T.R.; Cha, D.Y. Tetrahedron Lett. 1976, 1973-1976. After allowing for the recovery of starting material, the nett yield approaches 100%.
19. 17. Calo, V.; Lopez, L.; Mincuzzi, A.; Pesce, G. Synthesis, 1976, 200-201.
20. 18. Krow, G.R. Tetrahedron, 1987, 43, 3-38. Tubiana, W.; Waegell, B. Angew. Chem. Int. Ed. 1972, 11, 640-641. Nakata, T.; Nomura, S.; Matsukara, H. Tetrahedron Lett. 1996, 37, 213-216.
21. 18. Krow, G.R. Tetrahedron, 1987, 43, 3-38. Tubiana, W.; Waegell, B. Angew. Chem. Int. Ed. 1972, 11, 640-641. Nakata, T.; Nomura, S.; Matsukara, H. Tetrahedron Lett. 1996, 37, 213-216.
22. 18. Krow, G.R. Tetrahedron, 1987, 43, 3-38. Tubiana, W.; Waegell, B. Angew. Chem. Int. Ed. 1972, 11, 640-641. Nakata, T.; Nomura, S.; Matsukara, H. Tetrahedron Lett. 1996, 37, 213-216.
23. 19. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. J. Chem. Soc., Chem Commun. 1995, 1935-1936.
24. 20. Stavely, H.E. J. Am. Chem. Soc. 1941, 63, 3127-3131. Shoppee, C.W.; Prins, D.A. Helv. Chim. Acta, 1943, 26, 201-224. Miller, T.C. J. Org. Chem. 1969, 34, 3829-3833.
25. 20. Stavely, H.E. J. Am. Chem. Soc. 1941, 63, 3127-3131. Shoppee, C.W.; Prins, D.A. Helv. Chim. Acta, 1943, 26, 201-224. Miller, T.C. J. Org. Chem. 1969, 34, 3829-3833.
26. 20. Stavely, H.E. J. Am. Chem. Soc. 1941, 63, 3127-3131. Shoppee, C.W.; Prins, D.A. Helv. Chim. Acta, 1943, 26, 201-224. Miller, T.C. J. Org. Chem. 1969, 34, 3829-3833.
27. 21. Turner, R.B. J. Am. Chem. Soc. 1953, 75, 3484-3488. Kirk, D.N.; Mudd, A. J. Chem. Soc. (C), 1970, 2045-2048.
28. 21. Turner, R.B. J. Am. Chem. Soc. 1953, 75, 3484-3488. Kirk, D.N.; Mudd, A. J. Chem. Soc. (C), 1970, 2045-2048.
29. 22. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
30. 23. Kutschabsky, L.; Adam, G. J. Chem. Soc., Perkin Trans I 1983, 1653-1655.
31. 24. Cf. McKinney, M.A.; Patel, P.P. J. Org. Chem. 1973, 38, 4059-4064.
32. 25. Cross, B.E. J. Chem. Soc. 1960, 3022-3038.
33. 26. Bridel, M.; Lavielle, R. Bull. Soc. Chim. Biol. 1931, 13, 781-796. Mosettig, E.; Lichti, H. J. Org. Chem. 1955, 20, 884-899. Mossetig, E.; Beglinger, U.; Dolder, F.; Lichti, H.; Quitt, P.; Waters, J.A. J. Am. Chem. Soc. 1963, 85, 2305-2309.
34. 26. Bridel, M.; Lavielle, R. Bull. Soc. Chim. Biol. 1931, 13, 781-796. Mosettig, E.; Lichti, H. J. Org. Chem. 1955, 20, 884-899. Mossetig, E.; Beglinger, U.; Dolder, F.; Lichti, H.; Quitt, P.; Waters, J.A. J. Am. Chem. Soc. 1963, 85, 2305-2309.
35. 26. Bridel, M.; Lavielle, R. Bull. Soc. Chim. Biol. 1931, 13, 781-796. Mosettig, E.; Lichti, H. J. Org. Chem. 1955, 20, 884-899. Mossetig, E.; Beglinger, U.; Dolder, F.; Lichti, H.; Quitt, P.; Waters, J.A. J. Am. Chem. Soc. 1963, 85, 2305-2309.