Versatile configuration-encoded strategy for rapid synthesis of 1,5-polyol stereoisomers

Organic Letters

Volumn 12, Issue 21, 2010, Pages 5016-5019

  Friestad, Gregory K ^a   Sreenilayam, Gopeekrishnan ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; POLYMER; POLYOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; TIME;

BIOLOGICAL PRODUCTS; MOLECULAR STRUCTURE; POLYMERS; STEREOISOMERISM; TIME FACTORS;

EID: 78049489289     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1021417     Document Type: Article

References (37)

1. Isolation, structure, and biological activity
2. Kamiyama, T.; Umino, T.; Fujisaki, N.; Fujimori, K.; Satoh, T.; Yamashita, Y.; Ohshima, S.; Watanabe, J.; Yokose, K. J. Antibiot. 1993, 46, 1039-1036
3. Kobayashi, Y.; Czechtizky, W.; Kishi, Y. Org. Lett. 2003, 5, 93-96
4. Satoh, T.; Kouns, W. C.; Yamashita, Y.; Kamiyama, T.; Steiner, B. Biochem. J. 1994, 301, 785-791 Synthetic studies: Bouzbouz, S.; Cossy, J. Org. Lett. 2004, 6, 3469-3472
5. Lira, R.; Roush, W. R. Org. Lett. 2007, 9, 533-536
6. Zhang, K.; Curran, D. P. Synlett 2010, 667-671
7. Kim, G.-S.; Zeng, L.; Alali, F.; Rogers, L. L.; Wu, F.-E.; McLaughlin, J. L.; Sastrodihardjo, S. J. Nat. Prod. 1998, 61, 432-436
8. Hayakawa, Y.; Kanamaru, N.; Morisaki, N.; Seto, H. Tetrahedron Lett. 1991, 32, 213-216
9. Tamotsu, F.; Keitaro, E.; Tomomitsu, S.; Hiroko, H.; Hirayasu, O.; Noriko, S.; Takeshi, F.; Hideo, N.; Yasuhiro, I. J. Antibiot. 2002, 55, 873-880
10. Mudur, S. V.; Gloer, J. B.; Wicklow, D. T. J. Antibiot. 2006, 59, 500-506
11. Satake, M.; Murata, M.; Yasumoto, T.; Fujita, T.; Naoki, H. J. Am. Chem. Soc. 1991, 113, 9859-9861
12. Murata, M.; Matsuoka, S.; Matsumori, N.; Paul, G. K.; Tachibana, K. J. Am. Chem. Soc. 1999, 121, 870-871
13. Paquette, L. A.; Chang, S.-K. Org. Lett. 2005, 7, 3111-3114
14. Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 1411-1414
15. BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451-1454
16. Plaza, A.; Baker, H. L.; Bewley, C. A. J. Nat. Prod. 2008, 71, 473-477
17. A novel liposomal circular dichroism method has been devised to address the difficult structural analyses: MacMillan, J. B.; Molinski, T. F. J. Am. Chem. Soc. 2004, 126, 9944-9945
18. Bode, S. E.; Wolberg, M.; Muller, M. Synthesis 2006, 557-588
19. Kimball, D. B.; Silks, L. A. Curr. Org. Chem. 2006, 10, 1975-1992
20. BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451-1454
21. Also see ref 1d
22. Flamme, E. M.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 13644-13645
23. Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 1411-1414
24. Also see ref 1e.
25. Oishi, T.; Kanemoto, M.; Swasono, R.; Matsumori, N.; Murata, M. Org. Lett. 2008, 10, 5203-5206
26. Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585
27. Qin, Y. C.; Liu, L.; Pu, L. Org. Lett. 2005, 7, 2381-2383
28. Configurations were assigned via MPA esters: Louzao, I.; Seco, J. M.; Quiñoá, E.; Riguera, R. Chem. Commun. 2006, 142, 2-1424
29. A control experiment detected no loss of enantiopurity in (R)- 1 after treatment with NaHMDS in THF and quenching with water.
30. Use of NaHMDS in refluxing benzene for metallation of O -alkylcyanohydrin: Stork, G.; Takahashi, T. J. Am. Chem. Soc. 1977, 99, 1275-1276
31. To our knowledge, selective metallation and/or Julia coupling of a sulfone bearing remote O -alkyl- or O -silylcyanohydrin functionality has not been previously reported.
32. 1H NMR resonance attributed to an olefin proton of the minor Z isomer, appearing upfield of the major olefin protons. In cases where such a resonance could not be integrated (either not present or not resolved), the ratio was recorded in Table 1 as >95:5.
33. Satoh, T.; Kouns, W. C.; Yamashita, Y.; Kamiyama, T.; Steiner, B. Biochem. J. 1994, 301, 785-791
34. Gudipati, V. Ph.D. Thesis, University of Pittsburgh, 2008. We thank Professor Dennis Curran for providing a copy of this thesis.
35. 2CHO by asymmetric cyanation and reduction with DIBAL-H. See Supporting Information.
36. 2CHO: Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20
37. Cink, R. D.; Forsyth, C. J. J. Org. Chem. 1997, 62, 5672-5673