First total synthesis of (-)-AL-2

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2335-2338

  Miyakoshi, Naoki ^a   Mukai, Chisato ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 EPOXY(2,4 HEXADIYNYLIDENE) 1,6 DIOXASPIRO[4.5]DECANE; ACETAL DERIVATIVE; CARBON DIOXIDE; CARBONYL DERIVATIVE; HYDROXYL GROUP; METHANOL; NATURAL PRODUCT; PALLADIUM; SPIRO COMPOUND; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERE; CATALYST; CHEMICAL MODIFICATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

ACETALS; ARTEMISIA; EPOXY COMPOUNDS; PALLADIUM; SPIRO COMPOUNDS; STEREOISOMERISM; TARTRATES;

EID: 0141629681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0300569     Document Type: Article

References (38)

1. For examples, see: (a) Bohlmann, F.; Herbst, P.; Arndt, C.; Schönowsky, H.; Gleinig, H. Chem. Ber. 1961, 94, 3193. (b) Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.; Herbst, P. Chem. Ber. 1964, 97, 1179. (c) Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: London, 1973. (d) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691. (e) Martínez, V.; Barbera, O.; Sánchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619. (f) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931. (g) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food Chem. 1998, 46, 5031.
2. For examples, see: (a) Bohlmann, F.; Herbst, P.; Arndt, C.; Schönowsky, H.; Gleinig, H. Chem. Ber. 1961, 94, 3193. (b) Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.; Herbst, P. Chem. Ber. 1964, 97, 1179. (c) Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: London, 1973. (d) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691. (e) Martínez, V.; Barbera, O.; Sánchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619. (f) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931. (g) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food Chem. 1998, 46, 5031.
3. For examples, see: (a) Bohlmann, F.; Herbst, P.; Arndt, C.; Schönowsky, H.; Gleinig, H. Chem. Ber. 1961, 94, 3193. (b) Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.; Herbst, P. Chem. Ber. 1964, 97, 1179. (c) Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: London, 1973. (d) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691. (e) Martínez, V.; Barbera, O.; Sánchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619. (f) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931. (g) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food Chem. 1998, 46, 5031.
4. For examples, see: (a) Bohlmann, F.; Herbst, P.; Arndt, C.; Schönowsky, H.; Gleinig, H. Chem. Ber. 1961, 94, 3193. (b) Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.; Herbst, P. Chem. Ber. 1964, 97, 1179. (c) Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: London, 1973. (d) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691. (e) Martínez, V.; Barbera, O.; Sánchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619. (f) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931. (g) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food Chem. 1998, 46, 5031.
5. For examples, see: (a) Bohlmann, F.; Herbst, P.; Arndt, C.; Schönowsky, H.; Gleinig, H. Chem. Ber. 1961, 94, 3193. (b) Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.; Herbst, P. Chem. Ber. 1964, 97, 1179. (c) Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: London, 1973. (d) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691. (e) Martínez, V.; Barbera, O.; Sánchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619. (f) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931. (g) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food Chem. 1998, 46, 5031.
6. For examples, see: (a) Bohlmann, F.; Herbst, P.; Arndt, C.; Schönowsky, H.; Gleinig, H. Chem. Ber. 1961, 94, 3193. (b) Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.; Herbst, P. Chem. Ber. 1964, 97, 1179. (c) Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: London, 1973. (d) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691. (e) Martínez, V.; Barbera, O.; Sánchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619. (f) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931. (g) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food Chem. 1998, 46, 5031.
7. For examples, see: (a) Bohlmann, F.; Herbst, P.; Arndt, C.; Schönowsky, H.; Gleinig, H. Chem. Ber. 1961, 94, 3193. (b) Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.; Herbst, P. Chem. Ber. 1964, 97, 1179. (c) Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: London, 1973. (d) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691. (e) Martínez, V.; Barbera, O.; Sánchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619. (f) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931. (g) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food Chem. 1998, 46, 5031.
8. For structure determination, see: (a) Wurz, G.; Hofer, O.; Sanz-Cervera, J. F.; Marco, J. A. Ann. Chem. 1993, 99. (b) Birnecker, W.; Wallnöfer, B.; Hoffer, O.; Greger, H. Tetrahedron 1988, 44, 267.
9. For structure determination, see: (a) Wurz, G.; Hofer, O.; Sanz-Cervera, J. F.; Marco, J. A. Ann. Chem. 1993, 99. (b) Birnecker, W.; Wallnöfer, B.; Hoffer, O.; Greger, H. Tetrahedron 1988, 44, 267.
10. Nakamura, Y.; Kawamoto, N.; Ohto, Y.; Torikai, K.; Murakami, A.; Ohigashi, H. Cancer Lett. 1999, 140, 37.
11. According to the IUPAC nomenclature system, (-)-AL-2 (2) should be described as (-)-(2E,3S,4R,5R)-3,4-epoxy-(2,4-hexadiynylidene)-1,6dioxaspiro[4.5]decane. This numbering system is used for the dioxaspiro compounds in this manuscript.
12. For synthetic studies on total synthesis, see: (a) Toshima, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron Lett. 1996, 37, 5707. (b) Toshima, H.; Aramaki, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron 1998, 54, 5531. (c) Toshima, H.; Aramaki, H.; Ichihara, A. Tetrahedron Lett. 1999, 40, 3587.
13. For synthetic studies on total synthesis, see: (a) Toshima, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron Lett. 1996, 37, 5707. (b) Toshima, H.; Aramaki, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron 1998, 54, 5531. (c) Toshima, H.; Aramaki, H.; Ichihara, A. Tetrahedron Lett. 1999, 40, 3587.
14. For synthetic studies on total synthesis, see: (a) Toshima, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron Lett. 1996, 37, 5707. (b) Toshima, H.; Aramaki, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron 1998, 54, 5531. (c) Toshima, H.; Aramaki, H.; Ichihara, A. Tetrahedron Lett. 1999, 40, 3587.
15. Bohlmann, F.; Florentz, G. Chem. Ber. 1966, 99, 990.
16. (a) Mukai, C.; Moharram, S. M.; Kataoka, O.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1995, 2849.
17. (b) Mukai, C.; Moharram, S. M.; Hanaoka, M. Tetrahedron Lett. 1997, 38, 2511.
18. (c) Mukai, C.; Moharram, S. M.; Azukizawa, S.; Hanaoka, M. J. Org. Chem. 1997, 62, 8095.
19. (d) Mukai, C.; Miyakoshi, N.; Hanaoka, M. J. Org. Chem. 2001, 66, 5875.
20. (a) Kato, K.; Yamamoto, Y.; Akita, H. Tetrahedron Lett. 2002, 43, 4915.
21. (b) Kato, K.; Yamamoto, Y.; Akita, H. Tetrahedron Lett. 2002, 43, 6587.
22. For similar palladium(II)-catalyzed reactions, see: (a) Utimoto, K. Pure Appl. Chem. 1983, 54, 1845. (b) Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127. (c) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816. (d) Okumoto, H.; Nishihara, S.; Nakagawa, H.; Suzuki, A. Synlett 2000, 217. (e) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764 and references therein.
23. For similar palladium(II)-catalyzed reactions, see: (a) Utimoto, K. Pure Appl. Chem. 1983, 54, 1845. (b) Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127. (c) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816. (d) Okumoto, H.; Nishihara, S.; Nakagawa, H.; Suzuki, A. Synlett 2000, 217. (e) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764 and references therein.
24. For similar palladium(II)-catalyzed reactions, see: (a) Utimoto, K. Pure Appl. Chem. 1983, 54, 1845. (b) Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127. (c) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816. (d) Okumoto, H.; Nishihara, S.; Nakagawa, H.; Suzuki, A. Synlett 2000, 217. (e) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764 and references therein.
25. For similar palladium(II)-catalyzed reactions, see: (a) Utimoto, K. Pure Appl. Chem. 1983, 54, 1845. (b) Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127. (c) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816. (d) Okumoto, H.; Nishihara, S.; Nakagawa, H.; Suzuki, A. Synlett 2000, 217. (e) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764 and references therein.
26. For similar palladium(II)-catalyzed reactions, see: (a) Utimoto, K. Pure Appl. Chem. 1983, 54, 1845. (b) Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127. (c) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816. (d) Okumoto, H.; Nishihara, S.; Nakagawa, H.; Suzuki, A. Synlett 2000, 217. (e) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764 and references therein.
27. 13C NMR experiments. See ref 9e.
28. Saito, S.; Kuroda, A.; Tanaka, K.; Kimura, R. Synlett 1996, 231.
29. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
30. Reaction was monitored under various conditions by changing the kinds of palladium(II) catalysts and oxidizing reagents as well as the amounts of catalysts and oxidizing reagents.
31. Mixture of diastereoisomers was obtained.
32. Structure of 15 was elucidated by spectral evidence. In particular, NOE experiments revealed no enhancement between the vinylic proton and H-3 or between H-4 and H-10. In the 3-related (4R,5S)-compounds, an enhancement between H-4 and H-10 was observed in the NOE experiments.
33. Exclusive formation of the (5R)-isomer might be tentatively explained by assuming that the reaction proceeds via oxonium intermediate 8.
34. Procedure similar to the conversion of 19 into 22 was employed.
35. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763.
36. Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924.
37. Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721.
38. Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Shioiri, T. Synlett. 1998, 35.