Establishment of the structure of pinpollitol by total synthesis of the proposed putative structures

Synlett

Volumn , Issue 5, 2005, Pages 769-772

  Sureshan, Kana M ^a   Murakami, Tomohiro ^a   Watanabe, Yutaka ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

Cyclitol; Inositol; Natural product; Regioselectivity; Total synthesis

Indexed keywords

1,2:4,5 DI O ISOPROPYLIDENE INOSITOL; 1,3 DI O METHYLINOSITOL; 1,4 DI O METHYLINOSITOL; ALICYCLIC HYDROXY COMPOUND; CYCLITOL; DIMETHYL ETHER; INOSITOL; INOSITOL 1,3,5 ORTHOFORMATE; INOSITOL DERIVATIVE; NATURAL PRODUCT; PINPOLLITOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ISOMER; NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 15944425417     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863752     Document Type: Article

References (30)

1. (a) Hinchliffe, K.; Irvine, R. Nature 1997, 390, 123.
2. (b) Phosphoinositides: Chemistry, Biochemistry and Biomedical Applications; Bruzik, K. S., Ed.; ACS Symposium Series 718, Oxford University Press: Oxford, 1999.
3. (c) Ferguson, M. A. J.; Williams, A. F. Annu. Rev. Biochem. 1988, 57, 285.
4. Pinitol: (a) Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439.
5. (b) Ley, S. V.; Sternfeld, F.; Taylor, S. Tetrahedron Lett. 1987, 28, 225.
6. (c) Ley, S. V.; Sternfeld, F. Tetrahedron 1989, 45, 3463.
7. (d) Jung, P. M. J.; Motherwell, W. B.; Williams, A. S. Chem. Commun. 1997, 1283.
8. Ononitol: (e) Pietrusiewicz, K. M.; Salamonczyk, G. M. Synth. Commun. 1995, 25, 1863.
9. Quebrachitol: (f) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672.
10. Gallagher, R. T. Phytochemistry 1975, 14, 755.
11. Sureshan, K. M.; Shashidhar, M. S.; Praveen, T.; Das, T. Chem. Rev. 2003, 103, 4477.
12. Diketal 4 can be synthesized from myo-inositol in one step. See: Gigg, J.; Gigg, R.; Payne, S.; Conant, R. Carbohydr. Res. 1985, 142, 132.
13. Sureshan, K. M.; Yamasaki, T.; Hayashi, M.; Watanabe, Y. Tetrahedron: Asymmetry 2003, 14, 1771; and references cited therein.
14. Crystallographic data are deposited as CCDC 236206. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
15. Lee, H. W.; Kishi, Y. J. Org. Chem. 1985, 69, 4402.
16. Westerduin, P.; Willems, H. A. M.; van Boeckel, C. A. A. Tetrahedron Lett. 1990, 31, 6915.
17. (a) Kwon, Y.-K.; Lee, C.; Chung, S.-K. J. Org. Chem. 2002, 67, 3327.
18. (b) Suzuki, T.; Suzuki, S. T.; Yamada, I.; Koashi, Y.; Yamada, K.; Chida, N. J. Org. Chem. 2002, 67, 2874.
19. (c) Chida, N.; Ogawa, S. Chem. Commun. 1997, 807; and references cited therein.
20. (d) Suzuki, T.; Tanaka, S.; Yamada, I.; Koashi, Y.; Yamada, K.; Chida, N. Org. Lett. 2000, 2, 1137.
21. (e) Chida, N.; Yoshinaga, M.; Tobe, T.; Ogawa, S. Chem. Commun. 1997, 1043.
22. (f) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831.
23. Sureshan, K. M.; Shashidhar, M. S.; Varma, A. J. J. Org. Chem. 2002, 67, 6884; and references cited therein.
24. (a) Hosoda, A.; Miyake, Y.; Nomura, E.; Taniguchi, H. Chem. Lett. 2003, 32, 1042.
25. (b) Watanabe, Y.; Miyasou, T.; Hayashi, M. Org. Lett. 2004, 6, 1547.
26. (c) Sureshan, K. M.; Yamaguchi, K.; Sei, Y.; Watanabe, Y. Eur. J. Org. Chem. 2004, 4703.
27. Akiyama, T.; Hara, M.; Fuchibe, K.; Sakamoto, S.; Yamaguchi, K. Chem. Commun. 2003, 1734.
28. Sureshan, K. M.; Gonnade, R. G.; Shashidhar, M. S.; Puranik, V. G.; Bhadbhade, M. M. Chem. Commun. 2001, 881.
29. (a) Akiyama, T.; Nishimoto, H.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1992, 447.
30. (b) Akiyama, T.; Horiguchi, N.; Ida, T.; Ozaki, S. Chem. Lett. 1995, 975.