Synthesis of pyrenolide D analogues

Synlett

Volumn , Issue 14, 2008, Pages 2083-2086

  Robertson, Jeremy ^a   Stevens, Kiri ^a   Naud, Sébastien ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Butenolides; Furans; Lactones; Oxidations; Spiro compounds

Indexed keywords

ANTIFUNGAL AGENT; FURAN; GLUCOSE; HYDROXYL GROUP; LACTONE DERIVATIVE; PYRENOLIDE D; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CONTROLLED STUDY; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HUMAN; HUMAN CELL; IC 50; STEREOISOMERISM;

EID: 51149093492     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077976     Document Type: Article

References (28)

1. Nukina, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1988, 30, 57.
2. Nukina, M.; Hirota, H. Biosci., Biotechnol., Biochem. 1992, 56, 1158.
3. Engstrom, K. M.; Mendoza, M. R.; Navarro-Villalobos, M.; Gin, D. Y. Angew. Chem. Int. Ed. 2001, 40, 1128.
4. Robertson, J.; Meo, P.; Dallimore, J. W. P.; Doyle, B. M.; Hoarau, C. Org. Lett. 2004, 6, 3861.
5. (a) Bohlmann, F.; Jastrow, H.; Ertinghausen, G.; Kramer, D. Chem. Ber. 1964, 97, 801.
6. (b) Bohlmann, F.; Diedrich, B.; Gordon, W.; Fanghänel, L.; Schneider, J. Tetrahedron Lett. 1965, 1385.
7. (c) Bohlmann, F.; Fanghänel, L.; Kleine, K.-M.; Kramer, H.-D.; Mönch, H.; Schuber, J. Chem. Ber. 1965, 98, 2596.
8. For example: (a) Fukuda, H.; Takeda, M.; Sato, Y.; Mitsunobu, O. Synthesis 1979, 368.
9. (b) DeShong, P.; Waltermire, R. E.; Ammon, H. L. J. Am. Chem. Soc. 1988, 110, 1901.
10. (c) Kocienski, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1998, 9.
11. (d) Bartlett, S.; Hodgson, R.; Holland, J. M.; Jones, M.; Kilner, C.; Nelson, A.; Warriner, S. Org. Biomol. Chem. 2003, 1, 2393.
12. Lomas, A.; Robertson, J. unpublished results.
13. Bozó, E.; Boros, S.; Kuszmann, J.; Gács-Baitz, E.; Párkányi, L. Carbohydr. Res. 1998, 308, 297.
14. Knapp, S.; Madduru, M. R.; Lu, Z.; Morriello, G. J.; Emge, T. J.; Doss, G. A. Org. Lett. 2001, 3, 3583.
15. First described: Czernecki, S.; Gorson, G. Tetrahedron Lett. 1978, 4113.
16. Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622.
17. The preparation of this compound was first described (in outline) in: Horita, K.; Nagato, S.; Oikawa, Y.; Yonemitsu, O. Tetrahedron Lett. 1987, 28, 3253.
18. (a) Zhdanov, Y. A.; Alekseeva, V. G.; Korol, E. L. Dokl. Akad. Nauk SSSR 1975, 225, 1336.
19. (b) Grzeszczyk, B.; Dziewiszek, K.; Jarosz, S.; Zamojski, A. Carbohydr. Res. 1985, 145, 145.
20. (c) Sharma, G. V. M.; Hymavathi, L.; Krishna, P. R. Tetrahedron Lett. 1997, 38, 6929.
21. (d) Lubineau, A.; Gavard, O.; Alais, J.; Bonnaffe, D. Tetrahedron Lett. 2000, 41, 307.
22. The propensity for activation of positions α to furan under similar conditions has been demonstrated by us and others; for example: Harwood, L. M.; Robertson, J. Tetrahedron Lett. 1987, 28, 5175.
23. All reactions were run at 20°C except where stated.
24. Lipshutz, B. H.; Pollart, D.; Monforte, J.; Kotsuki, H. Tetrahedron Lett. 1985, 26, 705.
25. Pilcher, A. S.; DeShong, P. J. Org. Chem. 1993, 58, 5130.
26. Elend, D.; Fray, J.; Pryde, D. ARKIVOC 2006, (xi), 114.
27. For example: Paterson, I.; Anderson, E. A.; Dalby, S. M.; Loiseleur, O. Org. Lett. 2005, 7, 4125.
28. NMR assignments are numbered according to carbohydrate conventions (as Figure 1). Only strong or characterising IR peaks are given.