Total synthesis of (+)-cylindricine C

Tetrahedron Letters

Volumn 45, Issue 30, 2004, Pages 5921-5924

  Arai, Toshiharu ^a   Abe, Hideki ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Azaspirocyclization; Cyclic imine; Cylindricine; Grignard reaction; Intramolecular Michael addition

Indexed keywords

BROMINE 77; CYLINDRICINE C; ENAMINE; FLUORINE; NITROGEN; PYROGLUTAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; GRIGNARD REACTION; MICHAEL ADDITION; MOLECULE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 3242808880     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.142     Document Type: Article

References (18)

1. For recent reviews on marine natural products, see: Faulkner D.J. Nat. Prod. Rep. 17:2000;7-55
2. Faulkner D.J. Nat. Prod. Rep. 18:2001;1-49
3. Faulkner D.J. Nat. Prod. Rep. 19:2002;1-48
4. Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., Prinsep M.R. Nat. Prod. Rep. 21:2004;1-49
5. Blackman A.J., Li C., Hockless D.C.R., Skelton B.W., White A.H. Tetrahedron. 49:1993;8645-8656
6. Li C., Blackman A.J. Aust. J. Chem. 47:1994;1355-1361
7. Li C., Blackman A.J. Aust. J. Chem. 48:1995;955-965
8. Biard J.F., Guyot S., Roussakis C., Verbist J.F., Vercauteren J., Weber J.F., Boukef K. Tetrahedron Lett. 35:1994;2691-2694
9. Synthesis of (-)-cylindricine C: Molander G.A., Rönn M. J. Org. Chem. 64:1999;5183-5187
10. Synthesis of (+)-cylindricine C, D, and E: Trost B.M., Rudd M.T. Org. Lett. 5:2003;4599-4602
11. Abe H., Aoyagi S., Kibayashi C. Angew. Chem., Int. Ed. 41:2002;3017-3020
12. Little R.D., Masjedizadeh M.R., Wallquist O., McLoughlin J.I. Org. React. 47:1995;315-552
13. Katoh T., Nagata Y., Kobayashi Y., Arai K., Minami J., Terashima S. Tetrahedron Lett. 34:1993;5743-5746
14. Katoh T., Nagata Y., Kobayashi Y., Arai K., Minami J., Terashima S. Tetrahedron. 50:1994;6221-6238
15. For the organometallic ring-opening reaction of N-alkoxycarbonyl lactams, see: Giovannini A., Savoia D., Umani-Ronchi A. J. Org. Chem. 54:1989;228-234
16. On basic treatment of 18 and 20, ring opening is considered to take place via the following sequence involving retro-Michael addition generating the α,β-unsaturated aldehyde ii
17. The stereostructures of the allylated products 10 and 11 were assigned based on NOESY spectra which showed correlations between the C2-methyl protons and H5 for 10, and the C5-allyl methylene protons and H5 for 11
18. ax at 3.80 ppm, indicating their trans diaxial relationship and, hence, the C6 formyl group existing in an equatorial position (β configuration) on the cyclohexane ring