Concise asymmetric total synthesis of ent -guadinomic acid from an epoxy alkenol

Synlett

Volumn , Issue 18, 2009, Pages 2949-2952

  Kim, Hyemi ^a   Kim, Myung Yeol ^a   Tae, Jinsung ^a  

^a Yonsei University   (South Korea)

Author keywords

Cyclic guanidine; Epoxides; Guadinomic acid; Meta thesis; Total synthesis

Indexed keywords

ACRYLIC ACID; ALKENE; ALKENE DERIVATIVE; AZIDE; EPOXIDE; EPOXY ALKENOL; GUADINOMIC ACID; GUANIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CROSS LINKING; CYCLIZATION; HYDROLYSIS KINETICS; HYDROLYTIC KINETIC RESOLUTION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 72049117098     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218003     Document Type: Article

References (26)

1. Iwatsuki M, Uchida R, Yoshijima H, Ui H, Shiomi K, Matsumoto A, Takahashi Y, Abe A, Tomoda H, Omura S, J. Antibiot. 2008 61 222
2. Lingington R G., Robertson M, Gauthier A, Finlay B B., Soest R V., Andersen R J., Org. Lett. 2002 4 4089
3. Iwatsuki M, Uchida R, Yoshijima H, Ui H, Shiomi K, Kim Y.-P, Hirose T, Sunazuka T, Abe A, Tomoda H, Omura S, J. Antibiot. 2008 61 230
4. Tsuchiya S, Sunazuka T, Hirose T, Mori R, Tanaka T, Iwatsuki M, Omura S, Org. Lett. 2006 8 5577
5. Hirose T, Sunazuka T, Tsuchiya S, Tanaka T, Kojima Y, Mori R, Iwatsuki M, Omura S, Chem. Eur. J. 2008 14 8220
6. Kuwahara A, Nishikiori T, Shimada N, Nakagawa T, Fukazawa H, Mizuno S, Uehara Y, J. Antibiot. 1997 50 712
7. Horii S, Kameda Y, J. Antibiot. 1968 11 665
8. Singh M P., Petersen P J., Weiss W J., Janso J E., Luckman S W., Lenoy E B., Bradford P A., Testa R T., Greenstein M, Antimicrob. Agents Chemother. 2003 47 62
9. Fellows L E., Hider R C., Bell E A., Phytochemistry 1977 16 1957
10. Matsunaga S, Moore R E., Niemczura W P., Carmichael W P., J. Am. Chem. Soc. 1989 111 8021
11. (a) Kim Y.-J, Tae J, Synlett 2006 61
12. (b) Lee J, Jung Y.-H, Tae J, Bull. Korean Chem. Soc. 2007 28 513
13. (c) Jung Y.-H, Lee J, Tae J, Chem. Asian J. 2007 2 656
14. (d) Kim M.-Y, Kim H, Tae J, Synlett 2009 1303
15. Connon S J., Blechert S, Angew. Chem. Int. Ed. 2003 42 1900
16. Sabitha G, Babu R S., Rajkumar M, Yadav J S., Org. Lett. 2002 4 343
17. (a) Crotti P, Di Bussolo V, Favero L, Macchia F, Pineschi M, Eur. J. Org. Chem. 1998 1675
18. (b) Nugent T C., Hudlicky T, J. Org. Chem. 1998 63 510
19. (c) Chini M, Crotti P, Macchia F, Tetrahedron Lett. 1990 31 5641
20. (d) Scriven E F. V., Turnbull K, Chem. Rev. 1988 88 297
21. The reason for the improvement of the regioselectivity is not clear.
22. (a)Baker T J., Tomioka M, Goodman M, Org. Synth. 2002 78 91
23. (b) Feichtinger K, Zapf C, Sings H L., Goodman M, J. Org. Chem. 1998 63 3804
24. (c) Feichtinger K, Sings H L., Baker T J., Matthews K, Goodman M, J. Org. Chem. 1998 63 8432
25. McLaughlin M, Palucki M, Davies I W., Org. Lett. 2006 8 3311, Dhar D N., Murthy K S. K., Synthesis 1986 437
26. Enders D, Fey P, Kipphardt H, Org. Synth. 1987 65 173