Synthesis of spiroketals related to griseusin A

Molecules

Volumn 1, Issue 1, 1996, Pages 3-14

  Brimble, Margaret A ^a   Nairn, Michael R ^b  

^a UNIVERSITY OF SYDNEY   (Australia)

^b MASSEY UNIVERSITY   (New Zealand)

Author keywords

Antibiotics; Ceric ammonium nitrate; Furonaphthofuran; Furonaphthopyran; Pyranonaphthoquinone; Spiroketals

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 (5 TERT BUTYLDIMETHYLSILYLOXY 1 OXOHEX 2 ENYL) 1,4 NAPHTHOQUINONE; 2 (5 TERT BUTYLDIMETHYLSILYLOXY 1 OXOHEX 2 YNYL) 1,4 NAPHTHOQUINONE; 2 TRIMETHYLSILYL 3 (2 TERT BUTYLDIMETHYLSILYLOXYPROPYL) 9A,12A DIHYDRO 1H FURO[2'',3'':4',5']FURO[3',2':3,4]NAPHTHO[1,2 B]PYRAN 1,11(10H) DIONE; 2 TRIMETHYLSILYLOXYFURAN; 3 (2 TERT BUTYLDIMETHYLSILYLOXYPROPYL) 9A,12A DIHYDRO 1H FURO[2'',3'':4',5']FURO[3',2':3,4]NAPHTHO[1,2 B]PYRAN 1,11(10H) DIONE; 3,3A,5,11B TETRAHYDRO 5 HYDROXY 5 (4 HYDROXYPENT 1 ENYL) 2H FURO[3,2 B]NAPHTHO[2,3 D]PYRAN 2,6,11 TRIONE; 3,3A,5,11B TETRAHYDRO 5 HYDROXY 5 (4 TERT BUTYLDIMETHYLSILYLOXYPENT 1 ENYL) 2H FURO[3,2 B]NAPHTHO[2,3 D]PYRAN 2,6,11 TRIONE; 3A,11B,5',6' TETRAHYDRO 6' METHYLSPIRO[5H FURO[3,2 B]NAPHTHO[2,3 D]PYRAN 5',2' [2H]PYRAN] 2,6,11(3H) TRIONE; 3A,5A,11A,11B,5',6' HEXAHYDRO 5A,11A DIHYDROXY 6' METHYLSPIRO[5H FURO[3,2 B]NAPHTHO[2,3 D]PYRAN 5',2' [2H]PYRAN] 2,6,11(3H) TRIONE; 6 (5 TERT BUTYLDIMETHYLSILYLOXY 1 OXOHEX 2 ENYL) 6B,9A DIHYDRO 5 HYDROXYFURO[3,2 B]NAPHTHO[2,1 D]FURAN 8(9H) ONE; AMMONIUM DERIVATIVE; ANTIINFECTIVE AGENT; FURAN DERIVATIVE; GRISEUSIN A 1; KETONE DERIVATIVE; PHENOL; PYRANONAPHTHOQUINONE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ADDITION REACTION; ARTICLE; CHEMICAL BOND; DRUG SYNTHESIS; HYDROXYLATION; METHODOLOGY; MICHAEL ADDITION; OXIDATION; REACTION ANALYSIS;

EID: 0002422192     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.1007/s007830050002     Document Type: Article

References (24)

1. (a) Tsuji, N.; Kobayashi, M.; Wakisaka, Y.; Kawamura, Y.; Mayama, M.; Matsumoto, K. J. Antibiot., 1976, 29, 7.
2. (b) Tsuji, N.; Kobayashi, Y.; Terui, Y.; Tori, K. Tetrahedron, 1976, 32, 2207.
3. Tsuji, N.; Kamiguchi, T.; Nakai, H.; Shiro, M. Tetrahedron Lett., 1983, 24, 389.
4. (a) Moore, H. W.; Science, 1977, 197, 527.
5. (b) Moore, H.W.; Czerniak, R. Med. Res. Rev., 1981, 1, 249.
6. (a) Kometani, T.; Takeuchi, Y.; Yoshii, E. J. Org. Chem., 1982, 47, 4725.
7. (b) Kometani, T.; Takeuchi, Y.; Yoshii, E. J. Org. Chem., 1983, 48, 2311.
8. Matsumoto, K.; Takeuchi, Y.; Takeda, K.; Yoshii, E. Heterocycles, 1981, 16, 1659.
9. Brimble, M. A.; Nairn, M. R. J. Chem. Soc., Perkin Trans I, 1992, 579.
10. Harvey, R. G.; Hahn, J-T.; Bukowsa, M.; Jackson, H. J. Org. Chem., 1990, 55, 6161.
11. Parker, K. A.; Koh, Y. J. Am. Chem. Soc., 1994, 116, 11149 and references cited therein.
12. Griffith, W. P.; Ley, S. V. Aldrichimica Acta, 1990, 23, 13.
13. (b) Ley, S. V.; Norman, J.; Griffith, Marsden, Synthesis, 1994, 639.
14. Kirby, A. J.; The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer-Verlag, New York, 1983.
15. (b) Juaristi, E.; Cuevas, G. Tetrahedron, 1992, 48, 5019.
16. Deslongchamps, P.; Rowan, D. D.; Pothier, N.; Sauve, T.; Saunders, J. K. Can. J. Chem., 1981, 59, 1132.
17. (b) Pothier, N.; Rowan, D. D.; Deslongchamps, P.; Saunders, J. K. Can. J. Chem., 1981, 59, 1132.
18. Pothier, N.; Goldstein, S.; Deslongchamps, P., Helv. Chim. Acta, 1992, 75, 604.
19. Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc., 1992, 114, 9434.
20. Shih, T. L.; Mrozik, H.; Holmes, M. A.; Fisher, M. H. Tetrahedron Lett., 1990, 31, 3529.
21. (a) Ray, R.; Matteson, D. S. Tetrahedron Lett., 1980, 21, 449.
22. (b) DeCamp, A. E., Mills, S. G.; Kawaguchi, A. T.; Desmond, R.; Reamer, R. A.; DiMichele, L.; Volante, R. P. J. Org. Chem., 1991, 56, 3564.
23. Bhusan, V.; Rathore, R.; Chandrasekaran, S. Synthesis, 1984, 431.
24. Rauhut, G.; Chandrasekhar, J.; Alex, A.; Beck, B.; Sauer, W.; Clark, T.; VAMP 5.6, available from Oxford Molecular, The Magdalen Centre, Oxford Science Park, Sandford on Thames, Oxford OX4 4GA, United Kingdom. The authors like to thank Henryette Roth for carrying out the calculations at the Centre for Computational Chemistry of the Friedrich-Alexander University Erlangen-Nuremberg.