Enantioselective total synthesis of briarellins E and F: The first total syntheses of briarellin diterpenes

Journal of the American Chemical Society

Volumn 125, Issue 22, 2003, Pages 6650-6652

  Corminboeuf, Olivier ^a,b   Overman, Larry E ^a   Pennington, Lewis D ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ACTELION PHARMACEUTICALS LTD   (Switzerland)

^c ARRAY BIOPHARMA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRIARELLIN E; BRIARELLIN F; DITERPENE; ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; ENANTIOSELECTIVITY; PRODUCT RECOVERY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ANIMALS; CNIDARIA; DITERPENES; ETHERS, CYCLIC; STEREOISOMERISM;

EID: 0038547883     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035445c     Document Type: Article

References (47)

1. Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48 and earlier reviews in this series.
2. (a) Sung, P.-J.; Chen, M.-C. Heterocycles 2002, 57, 1705-1715.
3. (b) Cóbar, O. M. Rev. Latinoam. Quim. 2000, 28, 46-54.
4. (c) Bernardelli, P.; Paquette, L. A. Heterocycles 1998, 49, 531-556.
5. (d) Rodríguez, A. Tetrahedron 1995, 51, 4571-4618.
6. (e) Coll, J. C. Chem. Rev. 1992, 92, 613-631.
7. (f) Wahlberg, I.; Eklund, A.-M. In Progress in the Chemistry of Organic Natural Products; Springer-Verlag: New York, 1992; Vol. 60, pp 1-141.
8. The only exceptions are the pachyclavulariaenones, see: (a) Wang, G.-H.; Sheu, J.-H.; Duh, C.-Y.; Chiang, M. Y. J. Nat. Prod. 2002, 65, 1475-1478. (b) Wang, G.-H.; Sheu, J.-H.; Chiang, M. Y.; Lee, T.-J. Tetrahedron Lett. 2001, 42, 2333-2336. (c) Sheu, J.-H.; Wang, G.-H.; Sung, P.-J.; Duh, C.-Y.; Chiang, M. Y. Tetrahedron 2001, 57, 7639-7648.
9. The only exceptions are the pachyclavulariaenones, see: (a) Wang, G.-H.; Sheu, J.-H.; Duh, C.-Y.; Chiang, M. Y. J. Nat. Prod. 2002, 65, 1475-1478. (b) Wang, G.-H.; Sheu, J.-H.; Chiang, M. Y.; Lee, T.-J. Tetrahedron Lett. 2001, 42, 2333-2336. (c) Sheu, J.-H.; Wang, G.-H.; Sung, P.-J.; Duh, C.-Y.; Chiang, M. Y. Tetrahedron 2001, 57, 7639-7648.
10. The only exceptions are the pachyclavulariaenones, see: (a) Wang, G.-H.; Sheu, J.-H.; Duh, C.-Y.; Chiang, M. Y. J. Nat. Prod. 2002, 65, 1475-1478. (b) Wang, G.-H.; Sheu, J.-H.; Chiang, M. Y.; Lee, T.-J. Tetrahedron Lett. 2001, 42, 2333-2336. (c) Sheu, J.-H.; Wang, G.-H.; Sung, P.-J.; Duh, C.-Y.; Chiang, M. Y. Tetrahedron 2001, 57, 7639-7648.
11. (a) Maia, L. F.; de A. Epifanio, R.; Eve, T.; Fenical, W. J. Nat. Prod. 1999, 62, 1322-1324.
12. (b) Harvell, C. D.; West, J. M.; Griggs, C. Invertebr. Reprod. Dev. 1996, 30, 239-247.
13. (c) Harvell, C. D.; Fenical, W.; Roussis, V.; Ruesink, J. L.; Griggs, C. C.; Greene, C. H. Mar. Ecol. Prog. Ser. 1993, 93, 165-173.
14. Ospina, C. A.; Rodríguez, A. D.; Ortega-Barria, E.; Capson, T. L. J. Nat. Prod. 2003, 66, 357-363.
15. (a) Rodríguez, A. D.; Cóbar, O. M. Tetrahedron 1995, 51, 6869-6880.
16. (b) Rodríguez, A. D.; Cóbar, O. M. Chem. Pharm. Bull. 1995, 43, 1853-1858.
17. Acetoxycladiell-7(16), 11-dien-3-ol (1) and cladiell-11-ene-3,6,7-triol: (a) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392. (b) MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044. Sclerophytin A (2): (c) Overman, L. E.; Pennington, L. D. Org. Lett. 2000, 2, 2683-2686. (d) Gallou, F.; MacMillan, D. W. C.; Overman, L. E.; Paquette, L. A.; Pennington, L. D.; Yang, J. Org. Lett. 2001, 3, 135-137 and ref 7b. Alcyonin (3): (e) Corminboeuf, O.; Overman, L. E.; Pennington, L. D. Org. Lett. 2003, 5, 1543-1546.
18. Acetoxycladiell-7(16), 11-dien-3-ol (1) and cladiell-11-ene-3,6,7-triol: (a) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392. (b) MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044. Sclerophytin A (2): (c) Overman, L. E.; Pennington, L. D. Org. Lett. 2000, 2, 2683-2686. (d) Gallou, F.; MacMillan, D. W. C.; Overman, L. E.; Paquette, L. A.; Pennington, L. D.; Yang, J. Org. Lett. 2001, 3, 135-137 and ref 7b. Alcyonin (3): (e) Corminboeuf, O.; Overman, L. E.; Pennington, L. D. Org. Lett. 2003, 5, 1543-1546.
19. Acetoxycladiell-7(16), 11-dien-3-ol (1) and cladiell-11-ene-3,6,7-triol: (a) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392. (b) MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044. Sclerophytin A (2): (c) Overman, L. E.; Pennington, L. D. Org. Lett. 2000, 2, 2683-2686. (d) Gallou, F.; MacMillan, D. W. C.; Overman, L. E.; Paquette, L. A.; Pennington, L. D.; Yang, J. Org. Lett. 2001, 3, 135-137 and ref 7b. Alcyonin (3): (e) Corminboeuf, O.; Overman, L. E.; Pennington, L. D. Org. Lett. 2003, 5, 1543-1546.
20. Acetoxycladiell-7(16), 11-dien-3-ol (1) and cladiell-11-ene-3,6,7-triol: (a) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392. (b) MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044. Sclerophytin A (2): (c) Overman, L. E.; Pennington, L. D. Org. Lett. 2000, 2, 2683-2686. (d) Gallou, F.; MacMillan, D. W. C.; Overman, L. E.; Paquette, L. A.; Pennington, L. D.; Yang, J. Org. Lett. 2001, 3, 135-137 and ref 7b. Alcyonin (3): (e) Corminboeuf, O.; Overman, L. E.; Pennington, L. D. Org. Lett. 2003, 5, 1543-1546.
21. Acetoxycladiell-7(16), 11-dien-3-ol (1) and cladiell-11-ene-3,6,7-triol: (a) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392. (b) MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044. Sclerophytin A (2): (c) Overman, L. E.; Pennington, L. D. Org. Lett. 2000, 2, 2683-2686. (d) Gallou, F.; MacMillan, D. W. C.; Overman, L. E.; Paquette, L. A.; Pennington, L. D.; Yang, J. Org. Lett. 2001, 3, 135-137 and ref 7b. Alcyonin (3): (e) Corminboeuf, O.; Overman, L. E.; Pennington, L. D. Org. Lett. 2003, 5, 1543-1546.
22. For a recent review, see: Fürstner, A. Chem. Rev. 1999, 99, 991-1045.
23. 3, rt (79%).
24. 3, rt (79%).
25. The antipode of 10 was prepared previously in four steps from -(+)-limonene: Fráter, G. Helv. Chim. Acta 1979, 62, 641-643.
26. The relative configuration of 11 was corroborated by single-crystal X-ray analysis.
27. Patel, D. V.; VanMiddlesworth, F.; Donaubauer, J.; Gannett, P.; Sih, C. J. J. Am. Chem. Soc. 1986, 108, 4603-4614.
28. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979-982.
29. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
30. Wulff, W. D.; Peterson, G. A.; Bauta, W. E.; Chan, D.-S.; Faron, F. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 277-279.
31. Seyferth, D. J. Am. Chem. Soc. 1957, 79, 2133-2136.
32. The configuration of the major epimer of 15 is assigned by analogy to a similar coupling in our synthesis of cladiellins, see ref 7b.
33. 2NNa; 3-(tert-butyldiphenylsiloxy)propanal, -20 °C → rt (41%). (b) t-BuLi, THF, -78 °C; DMF (93%).
34. 2NNa; 3-(tert-butyldiphenylsiloxy)propanal, -20 °C → rt (41%). (b) t-BuLi, THF, -78 °C; DMF (93%).
35. This acetal was an inconsequential mixture of four diastereomers.
36. Baggiolini, E.; Hamlow, H. P.; Schaffner, K. J. Am. Chem. Soc. 1970, 92, 4906-4921.
37. The tetrasubstituted alkene regioisomer (∼10%) formed in the deformylation step was removed by chromatography on silica gel.
38. Takai, K.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 3791-3795.
39. The minor epoxide stereoisomer (∼10%) was removed by chromatography on silica gel.
40. Giner, J.-L.; Faraldos, J. A. J. Org. Chem. 2002, 67, 4659-4666.
41. (a) To avoid interaction with the five-carbon side chain, the 1-methyl-2-siloxyethyl substituent adopts a pseudoaxial orientation that shields the convex face of the hexahydroisobenzofuran.
42. (b) The minor epoxide stereoisomer (∼10% yield) was removed by chromatography on silica gel and fully characterized (see the Supporting Information).
43. The β C11,C12 epoxide is an observable intermediate in this sequence.
44. Orita, A.; Sakamoto, K.; Hamada, Y.; Mitsutome, A.; Otera, J. Tetrahedron 1999, 55, 2899-2910.
45. Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073.
46. Orita, A.; Hamada, Y.; Nakano, T.; Toyoshima, S.; Otera, J. Chem.-Eur. J. 2001, 7, 3321-3327.
47. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.