Enantioselective synthesis of 10-epi-anamarine via an iterative dihydroxylation sequence

Organic Letters

Volumn 7, Issue 6, 2005, Pages 1069-1072

  Gao, Dong ^a   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10 EPIANAMARINE; 5,10 DIEPIANAMARINE; LACTONE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; DIHYDROXYLATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; STEREOCHEMISTRY;

HYDROXYLATION; LACTONES; MOLECULAR STRUCTURE; PYRONES; STEREOISOMERISM;

EID: 15944379143     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047322i     Document Type: Article

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23. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
24. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
25. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
26. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
27. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
28. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
29. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
30. For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For other uses of this pyranone formation in synthesis, see refs 5b-e and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235. (d) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. (e) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512-2514. (f) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. (g) Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. (h) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. (i) Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 539-541.
31. 2PHAL, see Scheme 3).
32. 4/NMO in MeOH only a single tetrol is produced.
33. In contract to our results for acetonide 14 and its corresponding diol. Smith observed excellent regiocontrol (> 10.1) in the dihydroxylation of related substituted epoxy-trienoates. Similarly, they observed no significant loss of stereocontrol in the mismatched (slower) case; see ref 6.
34. While this second route (Scheme 4) is shorter, we preferred the first route (Scheme 3) because of the ease of isolation of all the intermediates and the greater overall yield (33 vs 26%).
35. 2 reagent for this transformation; see refs 3a-d. We have found that the Leighton reagent works equally well in terms of stereochemical outcome and allows for a significantly simpler product isolation procedure; see ref 9.
36. 1H NMR of the corresponding Mosher esters, see: Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.