Synthetic study on naturally occurring acetylenic spiroacetal enol ethers: The first access to optically active 3,4-diacetoxy-2-formylmethylene- 1,6-dioxaspiro[4.5]decanes

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3587-3590

  Toshima, Hiroaki ^a   Aramaki, Hisateru ^a   Ichihara, Akitami ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHRYSANTHEMUM; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR OVERHAUSER EFFECT; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

CHRYSANTHEMUM;

EID: 0033617122     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00579-1     Document Type: Article

References (20)

1. 1. (a) Christencen, L. P. Phytochemistry 1992, 31, 7-49;
2. (b) Marco, J. A.; Sanz, J. F.; Jakupovic, J.; Huneck, S. Tetrahedron 1990, 46, 6931-6938;
3. (c) Wurz, G.; Hofer, O.; Sanz-Cervera, J. F.; Marco, J. A. Leibigs Ann. Chem. 1993, 99-101;
4. (d) Birnecker, W.; Wallnofer, B.; Hofer, O.; Greger, H. Tetrahedron 1988, 44, 267-276;
5. (e) Bohlmann, F.; Ates, N.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1982, 21, 2691-2697;
6. (f) Bohlmann, F.; Rode, K. M. Chem. Ber. 1966, 99, 2416-2418.
7. 2. (a) Martinez, V.; Barbera, O.; Sanchez-Parareda, J.; Marco, J. A. Phytochemistry 1987, 26, 2619-2624;
8. (b) Breinlich, J.; Scharnagel, K. Arzneim-Forsch. 1968, 18, 429-431;
9. (c) Tada, M.; Chiba, K. Agric. Biol. Chem. 1984, 48, 1367-1369.
10. 3. (a) Ohigashi, H.; Nakamura, Y.; Murakami, A. Food Style 21 1998, 2, 31-35 (in Japanese);
11. (b) Nakamura, Y.; Ohto, Y.; Murakami, A.; Jiwajinda, S.; Ohigashi, H. J. Agric. Food. Chem. 1998, 46, 5031-5036.
12. 4. (a) Toshima, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron Lett. 1996, 37, 5707-5710;
13. (b) Toshima, H.; Aramaki, H.; Furumoto, Y.; Inamura, S.; Ichihara, A. Tetrahedron 1998, 54, 5531-5544.
14. 5. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
15. 6. Jarosz, S.; Salanski, P.; Mach, M. Tetrahedron 1998, 54, 2583-2594. and references cited therein.
16. D) were obtained for all new compounds.
17. 8. Column: CHIRALCEL OD® (φ4.6 × 250 mm), Eluent: hexane/2-propanol = 95/5, Flow rate 1.0 ml/min, Detection: UV 254 nm.
18. 9. Kusumi, T. J. Synth. Org. Chem. Jpn. 1993, 51, 462-470 (in Japanese).
19. 10. Although β-elimination-products 18S and 18R as well as 17 were obtained as single geometric isomers, respectively, the geometry was not determined by spectroscopic method.
20. 11. From the results up to date, the diacetyl groups of 19E may be converted to another protective group to prevent elimination in the process of diynyl part construction.