Synthesis of the 11-membered ring of the marine alkaloids, madangamines

Tetrahedron Letters

Volumn 47, Issue 20, 2006, Pages 3489-3492

  Yoshimura, Yuta ^a   Inoue, Junji ^a   Yamazaki, Naoki ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

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

Author keywords

Alkaloid; Macrocyclization; Madangamine; N,O Acetalization

Indexed keywords

ALKALOID DERIVATIVE; CYCLOHEXANONE DERIVATIVE; MACROCYCLIC COMPOUND; MADANGAMINE; UNCLASSIFIED DRUG;

ACETALIZATION; AMINATION; ARTICLE; CROSS COUPLING REACTION; DRUG SYNTHESIS; REDUCTION;

EID: 33646037966     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.160     Document Type: Article

References (18)

1. Kong F., Andersen R.J., and Allen T.M. J. Am. Chem. Soc. 116 (1994) 6007-6008
2. Kong F., Graziani E.I., and Andersen R.J. J. Nat. Prod. 61 (1998) 267-271
3. Matzanke N., Gregg R.J., Weinreb S.M., and Parvez M. J. Org. Chem. 62 (1997) 1920-1921
4. Tong H.-M., Martin M.-T., Chiaroni A., Bénéchle M., and Marazano C. Org. Lett. 7 (2005) 2437-2440
5. Yamazaki N., Suzuki H., and Kibayashi C. J. Org. Chem. 62 (1997) 8280-8281
6. Suzuki H., Yamazaki N., and Kibayashi C. Tetrahedron Lett. 42 (2001) 3013-3015
7. Yamazaki N., Kusanagi T., and Kibayashi C. Tetrahedron Lett. 45 (2004) 6509-6512
8. For other methods of synthesis of 11 see:. Macquarrie D.J. Tetrahedron Lett. 39 (1998) 4125-4128
9. Subba Rao Y.V., De Vos D.E., and Jacobs P.A. Angew. Chem., Int. Ed. 36 (1997) 2661-2663
10. Manickam G., and Sundararajan G. Tetrahedron 55 (1999) 2721-2736
11. Ranu B.C., Saha M., and Bhar S. Synth. Commun. 27 (1997) 621-626
12. The configuration and conformation of 16 were determined by the coupling constants and NOESY spectra as shown below:{A figure is presented}.
13. During acetalization by acidic treatment (TMSCl-ethylene glycol), no regioisomerization of the α-hydroxy ketone was observed, but epimerization of carbinol carbon at C-2 occurred to result in a diastereomeric mixture of 17.
14. The configuration of 19 was determined by NOESY spectra as shown below:{A figure is presented}.
15. An extended reaction time resulted in the cleavage of the O-benzyl groups.
16. Still W.C., and Gennari C. Tetrahedron Lett. 24 (1983) 4405-4408
17. Valle L.D., Stille J.K., and Hegedus L.S. J. Org. Chem. 55 (1990) 3019-3023
18. 2), 125.5 (CH), 127.17 (two carbons, CH), 127.25 (two carbons, CH), 127.29 (two carbons, CH), 127.9 (CH), 128.16 (two carbons, CH), 128.19 (two carbons, CH), 134.4 (C), 138.9 (C), 139.2 (C).