Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton

Journal of Organic Chemistry

Volumn 69, Issue 25, 2004, Pages 8789-8795

  Takao, Ken Ichi ^a   Yasui, Hiroyuki ^a   Yamamoto, Shun ^a   Sasaki, Daisuke ^a   Kawasaki, Soujiro ^a   Watanabe, Gohshi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; OXIDATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALDOL REACTIONS; METATHESIS PRODUCTS;

OLEFINS;

1,3 BUTADIENE; 7 OXABICYCLO[2.2.1]HEPT 2 ENE; 9 OXABICYCLO[4.2.1]NONA 2,4 DIENE DERIVATIVE; ALCOHOL; BICYCLO COMPOUND; COMPOUND 1893A; MYCOEPOXYDIENE; NATURAL PRODUCT; PYRAN DERIVATIVE; PYRANONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CROSS METATHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY;

BRIDGED COMPOUNDS; CYCLOPARAFFINS; MOLECULAR CONFORMATION; PYRONES;

EID: 10044263386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048566j     Document Type: Article

References (54)

1. Cai, P.; McPhail, A. T.; Krainer, E.; Katz, B.; Pearce, C.; Boros, C.; Caceres, B.; Smith, D.; Houck, D. R. Tetrahedron Lett. 1999, 40, 1479-1482.
2. Oxygen-bridged dibenzocyclooctadiene lignans such as kadsulignans are known. See: Liu, J.-S.; Li, L. Phytochemistry 1995, 38, 241-245.
3. Chen, G.; Lin, Y.; Wen, L.; Vrijmoed, L. L. P.; Jones, E. B. G. Tetrahedron 2003, 59, 4907-4909. The whole stereochemistry of 1893B (3) has not been determined.
4. The first total synthesis of (±)-1 was published by us in a preliminary communication. See: Takao, K.; Watanabe, G.; Yasui, H.; Tadano, K. Org. Lett. 2002, 4, 2941-2943.
5. Recently, an elegant route to enantiopure 9-oxabicyclo[4.2.1]non-3-ene was reported. See: Paquette, L. A.; Kim, I. H.; Cunière, N. Org. Lett. 2003, 5, 221-223.
6. For recent reviews on olefin metathesis, see: (a) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
7. (b) Blechert, S.; Connon, S. J. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
8. (c) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611-622.
9. (d) Trnka, T. M.; Grubbs, R. H. Ace. Chem. Res. 2001, 34, 18-29.
10. (e) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
11. Lee, C. W.; Choi, T.-L.; Grubbs, R. H. J. Am. Chem. Soc. 2002, 124, 3224-3225.
12. Mon, M.; Kuzuba, Y.; Kitamura, T.; Sato, Y. Org. Lett. 2002, 4, 3855-3858.
13. Kulkarni, A. A.; Diver, S. T. Org. Lett. 2003, 5, 3463-3466.
14. (a) Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1948, 70, 1161-1166.
15. (b) Chem. Abstr. 1966, 65, 16924e-16925b.
16. Cinquin, C.; Schaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339-340.
17. Das, J.; Vu, T.; Harris, D. N.; Ogletree, M. L. J. Med. Chem. 1988, 31, 930-935.
18. The ee values of (+)- and (-)-10 were determined by chiral HPLC analysis after conversion into the corresponding p-tert-butyl-benzoates. The absolute stereochemistry of (+)-10 has been unambiguously determined by Bloch's group.11
19. Ray, R.; Matteson, D. S. Tetrahedron Lett. 1980, 21, 449-450.
20. 4,5 = 0 Hz) were observed. The fact indicated that the dihydroxylation occurred on the β-face of (-)-15 to provide exo-diol (-)-16.
21. 3SnH in the presence of AIBN gave a complex mixture.
22. Use of pyridine in place of the n-BuLi/THF system resulted in the undesired intramolecular cyclization of intermediary monotosylate, providing a 3,8-dioxabicyclo[3.2.1]octane derivative.
23. When tetrahydrofuran was used as the solvent, the reaction proceeded less effectively.
24. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
25. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
26. When 20 mol % of 21 was added in one portion, the product (+)-5 was obtained in 41% yield.
27. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
28. (a) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
29. (b) Arjona, O.; Csáky, A. G.; Murcia, M. C.; Plumet, J. J. Org. Chem. 1999, 64, 9739-9741. Also see refs 6b and 6c.
30. (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611.
31. (b) Michaut, M.; Parrain, J.-L.; Santelli, M. Chem. Commun. 1998, 2567-2568.
32. 2 occurred even after a prolonged reaction time.19b We presume that the vinylalkylidene ruthenium complex, which behaves as an active catalytic species, is initially formed. For the reaction mechanism of ROM/CM, see ref 23.
33. For discussions regarding the effect of solvent and reaction temperatures in metathesis, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207.
34. (b) Yamamoto, K.; Biswas, K.; Gaul, C.; Danishefsky, S. J. Tetrahedron Lett. 2003, 44, 3297-3299.
35. Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136.
36. Under the ROM/CM conditions described in Table 1, no formation of the 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton was observed.
37. It was confirmed that the ROM/CM of (-)-13 with use of 21 in benzene produced preferentially the Z-isomers (Z/E = 1.6:1).
38. For a review on furan as a building block in organic synthesis, see: Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, Germany, 1995; pp 231-242.
39. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
40. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
41. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
42. Ho, T.-L.; Sapp, S. G. Synth. Commun. 1983, 13, 207-211.
43. Reproducible results were obtained by a nonaqueous workup. For an example of water-unstable hemiacetal, see: Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902-5915.
44. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981,103, 5454-5459.
45. 3-13 (9.3%) were also observed.
46. The optical purity of synthetic (+)-1 was confirmed by chiral HPLC analysis to be 94%.
47. For a review regarding vinylogous aldol reactions, see: Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000,100, 1929-1972.
48. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037-4040.
49. The configurations of the two introduced stereogenic centers in each diastereomer of 46 could not be determined.
50. By using the mixture 46, the total synthesis of 1893B (3) was also investigated. But we have not succeeded in the synthesis of 3 from 46 yet. Synthetic studies of 3 are now in progress.
51. Pohmakotr, M.; Tuchinda, P.; Premkaisorn, P.; Reutrakul, V. Tetrahedron 1998, 54, 11297-11304.
52. 3-13 in (-)-2 was irradiated, a signal enhancement at H5 (4.5%) was also observed. It was confirmed that no epimerization at C6 occurred under Dess-Martin oxidation and/or the vinylogous aldol reaction conditions.
53. 13C NMR), see the Supporting Information.
54. Chen, G. Personal communication. They explained that their miscalculation caused this change.