Total synthesis of (-)-amathaspiramide F

Tetrahedron

Volumn 65, Issue 50, 2009, Pages 10355-10364

  Sakaguchi, Kazuhiko ^a   Ayabe, Miki ^a   Watanabe, Yusuke ^a   Okada, Takuya ^a   Kawamura, Kazushige ^a   Shinada, Tetsuro ^a   Ohfune, Yasufumi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Acyloxysilane; Amathaspiramide F; Enolate Claisen rearrangement; Heptamethyldisilazane; Tetrabutylammonium dichlorobromate

Indexed keywords

ALKALOID DERIVATIVE; AMATHASPIRAMIDE F; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CLAISEN REARRANGEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 70350736599     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.051     Document Type: Article

References (50)

1. Morris B.D., and Prinsep M.R. J. Nat. Prod. 62 (1999) 688-693
2. For several biologically active natural products containing cyclic spirolactam or hemiaminal structure:
3. Hirsutellone B., Isaka M., Rugseree N., Maithip P., Kongsaeree P., Prabpai S., and Thebtaranonth Y. Tetrahedron 61 (2005) 5577-5583
4. Massadine:. Nishimura S., Matsunaga S., Shibazaki M., Suzuki K., Furihata K., van Soest R.W.M., and Fusetani N. Org. Lett. 5 (2003) 2255-2257
5. Azaspirene:. Asami Y., Kakeya H., Onose R., Yoshida A., Matsuzaki H., and Osada H. Org. Lett. 4 (2002) 2845-2848
6. Axinellamine:. Urban S., Leone P.A., Carroll A.R., Fechner G.A., Smith J., Hopper J.N.A., and Quinn R.J. J. Org. Chem. 64 (1999) 731-735
7. Pseurotin A:. Komagata D., Fujita S., Yamashita N., Saito S., and Morino T. J. Antibiot. 49 (1996) 958-959
8. Synerazol:. Ando O., Satake H., Nakajima M., Sato A., Nakamura T., Kinoshita T., Furuya K., and Haneishi T. J. Antibiot. 44 (1991) 382-389
9. Hughes C.C., and Trauner D. Angew. Chem., Int. Ed. 41 (2002) 4556-4559
10. Sakaguchi K., Ayabe M., Watanabe Y., Okada T., Kawamura K., Shinada T., and Ohfune Y. Org. Lett. 10 (2008) 5449-5452
11. Sakaguchi K., Higashino M., and Ohfune Y. Tetrahedron 59 (2003) 6647-6658
12. Sakaguchi K., Yamada T., and Ohfune Y. Tetrahedron Lett. 46 (2005) 5009-5012
13. Sakaguchi K., Okada T., Yamada T., and Ohfune Y. Tetrahedron Lett. 48 (2007) 3925-3928
14. Sakaguchi K., Suzuki H., and Ohfune Y. Chirality 13 (2001) 357-365
15. Morimoto Y., Takanishi M., Kinoshita T., Sakaguchi K., and Shibata K. Chem. Commun. (2002) 42-43
16. Sakaguchi K., Yamamoto M., Kawamoto T., Yamada T., Shinada T., Shimamoto K., and Ohfune Y. Tetrahedron Lett. 45 (2004) 5869-5872
17. Sakaguchi K., Yamamoto M., Watanabe Y., and Ohfune Y. Tetrahedron Lett. 48 (2007) 4821-4824
18. 2-assisted dianionic enolate Claisen rearrangement of the N-protected α-amino acid allyl ester was originally developed by Kazmaier:. Kazmaier U. Angew. Chem., Int. Ed. Engl. 33 (1994) 998-999
19. The enolate Claisen rearrangement of (S)-α-acyloxy-α-vinylsilane having Boc-proline as the acyloxy group (>95% ee) (LHMDS (3 equiv), HMPA/THF (1:4), -78 °C to rt) gave the α-substituted proline with (S)-configuration (>95% ee), see Ref. 6d.
20. The chelation-controlled stereoselective enolate Claisen rearrangement of (E)-crotyl pyroglutamate using chiral ligands:. Kazmaier U., Mues H., and Krabs A. Eur. J. Chem. 8 (2002) 1850-1855
21. The diastereoselective enolate Claisen rearrangement of the 5-substituted-Boc-proline (E)-allylic ester:. Lee M., Lee T., Kim E.-Y., Ko H., Kim D., and Kim S. Org. Lett. 8 (2006) 745-748
22. Sakaguchi K., Fujita M., Suzuki H., Higashino M., and Ohfune Y. Tetrahedron Lett. 41 (2000) 6589-6592
23. Sonogashira K. In: Diederrich F., and Stang P.L. (Eds). Metal-catalyzed Cross-coupling Reactions (1998), Wiley-VCH, Weinheim Chapter 5
24. Liron F., Garrev P.L., and Alami M. Synlett (1999) 246-248
25. Nowick J.S., and Danheiser R.L. J. Org. Chem. 54 (1989) 2798-2802
26. Luche J.L. J. Am. Chem. Soc. 100 (1978) 2226-2227
27. It has been reported that the ozonolysis of the vinylsilane does not give the corresponding aldehyde, see:
28. Büchi G., and Wüest H. J. Am. Chem. Soc. 100 (1978) 294-295
29. Murakami M., Sakita K., Igawa K., and Tomooka K. Org. Lett. 8 (2006) 4023-4026
30. The calculation was performed by Spartan '04.
31. For examples of the [3,3] sigmatropic rearrangement that proceeded via the boat-like transition state, see:
32. Waetzig S.R., and Tunge J.A. J. Am. Chem. Soc. 129 (2007) 4138-4139
33. Lindstroem U.M., and Somfai P. Eur. J. Chem. 7 (2001) 94-98
34. Wipf P. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford 827
35. 6d According to the energy calculation results (Scheme 6), the E-enolate derived from (E)-5 would undergo the enolate Claisen rearrangement via both the transition states M and N to give the threo and erythro-6, respectively. Therefore, the moderate threo selectivity (dr 3.5:1) would be observed in the reaction of (E)-5 without HMPA.
36. 3 (1 equiv), acetone, rt, 15 h, 30%).
37. 1H NMR analysis of the reaction mixture.{A figure is presented}
38. 2, rt, 10 min) also gave the monobrominated product 18 in moderate yield (22-30%). The reaction of 17 with NBS (2 equiv) and TsOH (0.22 equiv) in DMF (rt, 18 h) afforded a trace amount of 18.
39. Matsuo J., Iida D., Yamanaka H., and Mukaiyama T. Tetrahedron 59 (2003) 6739-6750
40. Sonderquist E.J., Anderson C.L., Miranda E.I., and Rivera I. Tetrahedron Lett. 31 (1990) 4677-4680
41. Dahr R.K. Aldrichimica Acta 27 (1994) 43-51
42. The absolute configuration of the minor isomer was not determined.
43. 2 resulted in the decreased yield of 23 (28%).
44. The spirolactone 29 was obtained as a single diastereomer. The relative stereochemistry of 29 was not determined.
45. Lower amounts of methylamine (2 equiv) resulted in the decreased yield of 28 (<20%).
46. For the electrophilic 4,6-dibromination of 3-substituted phenol, see:
47. Osuna M.R., Agurrie G., Somanathan R., and Molins E. Tetrahedron: Asymmetry 13 (2002) 2261-2266
48. Hashimoto A., Jacobson A.E., Rothman R.B., Dersch C.M., George C., F-Anderson J.L., and Rice K.C. Bioorg. Med. Chem. 10 (2002) 3319-3329
49. Negoro T., Wada M., and Someya M. Bull. Fac. Edu. Wakayama Univ. Natur. Sci. 48 (1998) 1-7
50. 1