Stereoselective synthesis of (+)-IKD-8344

Tetrahedron

Volumn 63, Issue 39, 2007, Pages 9784-9801

  Kim, Woo Han ^a   Hong, Sung Kil ^a   Lim, Sang Min ^a   Ju, Min Ae ^a   Jung, Soon Kyu ^a   Kim, Yong Wook ^a   Jung, Jae Hoon ^a   Kwon, Min Sang ^a   Lee, Eun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

IKD 8344; MACROLIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIMERIZATION; DRUG SYNTHESIS; HORNER REACTION; MOLECULAR INTERACTION; OLEFINATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 34547821399     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.005     Document Type: Article

References (30)

1. For a recent review on total syntheses of oxacyclic macrodiolides, see:. Kang E.J., and Lee E. Chem. Rev. 105 (2005) 4348-4378
2. Minami Y., Yoshida K., Azuma R., Nishii M., Inagaki J., and Nohara F. Tetrahedron Lett. 33 (1992) 7373-7376
3. Ishida T., In Y., Nishii M., and Minami Y. Chem. Lett. 23 (1994) 1321-1322
4. Hwang E.I., Yun B.S., Yeo W.H., Lee S.H., Moon J.S., Kim Y.K., Lim S.J., and Kim S.U. J. Microbiol. Biotechnol. 15 (2005) 909-912
5. Jiang W., Lantrip D.A., and Fuchs P.L. Org. Lett. 2 (2000) 2181-2184
6. Kim W.H., Hong S.K., Lim S.M., Ju M.-A., Jung S.K., Kim Y.W., Jung J.H., Kwon M.S., and Lee E. Angew. Chem., Int. Ed. 45 (2006) 7072-7075
7. For example, there is a report on the asymmetric titanium aldol reactions involving cyclic oxocarbenium ion derived from (S)-glutamic acid, but we were not able to reproduce the results:. Pilli R.A., Riatto V.B., and Vencato I. Org. Lett. 2 (2000) 53-56
8. For an example of the use of this known aldehyde, see:. Smith III A.B., and Kim D.-S. J. Org. Chem. 71 (2006) 2547-2557
9. For an example of asymmetric aldol reactions, see:. Evans D.A., Kaldor S.W., Jones T.K., Clardy J., and Stout T.J. J. Am. Chem. Soc. 112 (1990) 7001-7031
10. See the following reference for detailed discussions:. Evans D.A., Allison B.D., Yang M.G., and Masse C.E. J. Am. Chem. Soc. 123 (2001) 10840-10852
11. It was best to keep the mesyloxy group until this point as the volatility problem arose when mesyloxy group was removed at an earlier stage.
12. For use of magnesium bromide etherate in allylstannane reaction, see:. Lee E., Jeong E.J., Kang E.J., Sung L.T., and Hong S.K. J. Am. Chem. Soc. 123 (2001) 10131-10132
13. Walkup R.D., and Obeyesekere N.U. Synthesis (1987) 607-611
14. For recent examples of β-alkoxyacrylate and β-alkoxymethacrylate radical cyclization, see:
15. Kang E.J., Cho E.J., Ji M.K., Lee Y.E., Shin D.M., Choi S.Y., Chung Y.K., Kim J.-S., Kim H.-J., Lee S.-G., Lah M.S., and Lee E. J. Org. Chem. 70 (2005) 6321-6329
16. Song H.Y., Joo J.M., Kang J.W., Kim D.-S., Jung C.-K., Kwak H.S., Park J.H., Lee E., Hong C.Y., Jeong S., Jeon K., and Park J.H. J. Org. Chem. 68 (2003) 8080-8087
17. Jeong E.J., Kang E.J., Sung L.T., Hong S.K., and Lee E. J. Am. Chem. Soc. 124 (2002) 14655-14662
18. Lee E., Choi S.J., Kim H., Han H.O., Kim Y.K., Min S.J., Son S.H., Lim S.M., and Jang W.S. Angew. Chem., Int. Ed. 41 (2002) 176-178
19. Lee E., and Choi S.J. Org. Lett. 1 (1999) 1127-1128
20. For examples for room temperature metallation of 2-substituted 1,3-dithiane derivatives, see:. Ide M., and Nakata M. Bull. Chem. Soc. Jpn. 72 (1999) 2491-2499
21. Matsushita M., Nagaoka Y., Hioki H., Fukuyama Y., and Kodama M. Chem. Lett. 25 (1996) 1039-1040
22. De Brabander J., Vanhessche K., and Vandewalle M. Tetrahedron Lett. 32 (1991) 2821-2824
23. For profitable use of PMB ethers in place of benzyl ethers, see the Ref. 15.
24. Kim W.H., Jung J.H., Sung L.T., Lim S.M., and Lee E. Org. Lett. 7 (2005) 1085-1087
25. For an example of the successful macrodiolide formation under similar conditions, see:. Fürstner A., Mlynarski J., and Albert M. J. Am. Chem. Soc. 124 (2002) 10274-10275
26. The spectral data of the synthetic sample were identical with those of the natural product.
27. For use of the modified Yamaguchi conditions, see:. Evans D.A., Ng H.P., and Rieger D.L. J. Am. Chem. Soc. 115 (1993) 11446-11459
28. Garber S.B., Kingsbury J.S., Gray B.L., and Hoveyda A.H. J. Am. Chem. Soc. 122 (2000) 8168-8179
29. Okada A., Ohshima T., and Shibasaki M. Tetrahedron Lett. 42 (2001) 8023-8027
30. Aggarwal V.K., and Daly A.M. Chem. Commun. (2002) 2490-2491