Asymmetric catalytic alkynylation of acetaldehyde: Application to the synthesis of (+)-tetrahydropyrenophorol

Angewandte Chemie - International Edition

Volumn 51, Issue 27, 2012, Pages 6704-6708

  Trost, Barry M ^a   Quintard, Adrien ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

alkynes; asymmetric catalysis; natural product synthesis; synthetic methods; zinc

Indexed keywords

ALDOLIZATION; ALKYNES; ALKYNYLATIONS; ASYMMETRIC CATALYSIS; ENANTIOCONTROL; IN-CONTROL; NATURAL PRODUCT SYNTHESIS; SYNTHETIC METHODS; SYNTHONS;

ACETYLENE; ZINC;

ACETALDEHYDE;

(5S,8R,13S,16R) ( ) PYRENOPHOROL; (5S,8R,13S,16R)-(-)-PYRENOPHOROL; ACETALDEHYDE; ALKYNE; HETEROCYCLIC COMPOUND; KETONE; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETALDEHYDE; ALKYNES; CATALYSIS; HETEROCYCLIC COMPOUNDS; KETONES; STEREOISOMERISM; ZINC;

EID: 84863223734     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203035     Document Type: Article

References (47)

1. K. Matsumura, S. Hashguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738
2. S. Hu, L. P. Hager, J. Am. Chem. Soc. 1999, 121, 872
3. A. Ford, S. Woodward, Angew. Chem. 1999, 111, 347
4. Angew. Chem. Int. Ed. 1999, 38, 335
5. A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, S. Woodward, Chem. Eur. J. 2000, 6, 3586
6. C. F. Thompson, T. F. Jamison, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 9974
7. N. Pétry, A. Parenty, J.-M. Campagne, Tetrahedron: Asymmetry 2004, 15, 1199
8. V. B. Birman, L. Guo, Org. Lett. 2006, 8, 4859
9. R. S. Coleman, X. Lu, I. Modolo, J. Am. Chem. Soc. 2007, 129, 3826
10. Y. Xing, G. A. Doherty, Org. Lett. 2009, 11, 1107. For a review dealing with the preparation of enantioenriched compound with a methyl substituent, see
11. K. Endo, T. Shibata, Synthesis 2012, DOI:.
12. For a recent review, see:, B. M. Trost, A. H. Weiss, Adv. Synth. Catal. 2009, 351, 963.
13. D. E. Frantz, R. Fassler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806
14. N. K. Anand, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 9687
15. G. Lu, X. Li, W. L. Chan, A. S. C. Chan, Chem. Commun. 2002, 172
16. G. Gao, D. Moore, R.-G. Xie, L. Pu, Org. Lett. 2002, 4, 4143
17. S. Reber, T. N. Knopfel, E. M. Carreira, Tetrahedron 2003, 59, 6813
18. T. Xu, C. Liang, Y. Cai, J. Li, Y.-M. Li, X.-P. Hui, Tetrahedron: Asymmetry 2009, 20, 2733
19. Y. Yue, M. Turlington, X.-Q. Yu, L. Pu, J. Org. Chem. 2009, 74, 8681
20. B. M. Trost, V. S. Chan, D. Yamamoto, J. Am. Chem. Soc. 2010, 132, 5186
21. Y. Du, M. Turlington, X. Zhou, L. Pu, Tetrahedron Lett. 2010, 51, 5024
22. M. Turlington, Y. Du, S. G. Ostrum, V. Santosh, K. Wren, T. Lin, M. Sabat, L. Pu, J. Am. Chem. Soc. 2011, 133, 11780
23. N. Kojima, S. Nishijima, K. Tsuge, T. Tanaka, Org. Biomol. Chem. 2011, 9, 4425
24. R. Boobalan, C. Chen, G.-H. Lee, Org. Biomol. Chem. 2012, 10, 1625
25. B. M. Trost, M. J. Bartlett, Org. Lett. 2012, 14, 1322
26. B. M. Trost, A. C. Burns, M. Bartlett, T. Tautz, A. H. Weiss, J. Am. Chem. Soc. 2012, 134, 1474
27. M. Turlington, L. Pu, Synlett 2012, 23, 649.
28. B. J. Albert, A. Sivaramakrishnan, T. Naka, K. Koide, J. Am. Chem. Soc. 2006, 128, 2792
29. B. J. Albert, A. Sivaramakrishnan, T. Naka, N. L. Czaicki, K. Koide, J. Am. Chem. Soc. 2007, 129, 2648
30. D. Beatriz, PCT, WO2004092098, 2004.
31. B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003; For the first use of the ProPhenol system in aldehyde alkynylation
32. B. M. Trost, A. H. Weiss, A. J. von Wangelin, J. Am. Chem. Soc. 2006, 128, 8.
33. 3PO ratio might better be explained by a Lewis base concentration effect playing on its ability to compete with acetaldehyde coordination.
34. See Refs. [4a,b] and:, B. M. Trost, T. J. J. Muller, J. Martinez, J. Am. Chem. Soc. 1995, 117, 1888.
35. G. Sabitha, C. S. Reddy, J. S. Yadav, Tetrahedron Lett. 2006, 47, 4513. For another shorter synthesis of this natural product
36. B. W. Gung, H. Dickson, Org. Lett. 2002, 4, 2517.
37. K. Krohn, U. Farooq, U. Florke, B. Schulz, S. Draeger, G. Pescitelli, P. Slavadori, S. Antus, T. Kurtan, Eur. J. Org. Chem. 2007, 3206, and references herein.
38. F. J. Dommerholt, L. Thijs, B. Zwanenburg, Tetrahedron Lett. 1991, 32, 1499
39. N. Machinaga, C. Kibayashi, Tetrahedron Lett. 1993, 34, 841
40. S. Amigoni, Y. Le Floc'h, Tetrahedron: Asymmetry 1997, 8, 2827
41. J. S. Yadav, U. V. Subba Reddy, B. V. Subba Reddy, Tetrahedron Lett. 2009, 50, 5984
42. J. S. Yadav, G. M. Reddy, T. S. Rao, B. V. S. Reddy, A. Al Khazim Al Ghamdi, Synthesis 2012, 783; For the synthesis of pyrenophorol (15 steps) and tetrahydropyrenophorol (16 steps), see
43. H.-S. Oh, H.-Y. Kang, Bull. Korean Chem. Soc. 2011, 32, 2869. For an early approach to chiral 1,4-diols through aldehyde asymmetric alkynylation, see
44. M. Amador, X. Arisa, J. Garcia, J. Ortiz, Tetrahedron Lett. 2002, 43, 2691.
45. B. M. Trost, J. D. Chisholm, Org. Lett. 2002, 4, 3743.
46. H. Gerlach, K. Gertle, A. Thanann, Helv. Chim. Acta 1977, 60, 2860.
47. For the mild THP protection/removal method, see:, M. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem. 1977, 42, 3772. It is worth mentioning that 3-butyn-2-ol, easily obtained in two steps by this sequence, is a rather expensive commercially available compound (Alrich: 1 g (R) enantiomer=142.5 USD, 1 g (S) enantiomer=214.5 USD).