Synthesis of (-)-isonitrin B

Journal of the American Chemical Society

Volumn 120, Issue 51, 1998, Pages 13285-13290

  Taber, Douglass F ^a   Yu, Han ^a   Dincarvito, Christopher ^a   Rheingold, Arnold L ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ISONITRILE DERIVATIVE; ISONITRIN B; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0032583580     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981700v     Document Type: Article

References (18)

1. For isolation and physiological activity, see: (a) Fujiwara, A.; Okuda, T.; Masuda, S.; Shiomi, Y.; Miyamoto, C.; Sekine, Y.; Tazoe, M.; Fujiware, M. Agric. Biol. Chem. 1982, 46, 1803. (b) Okuda, T.; Fujiwara, A., Fujiwara, M. Agric. Biol. Chem. 1982, 46, 1811.
2. For isolation and physiological activity, see: (a) Fujiwara, A.; Okuda, T.; Masuda, S.; Shiomi, Y.; Miyamoto, C.; Sekine, Y.; Tazoe, M.; Fujiware, M. Agric. Biol. Chem. 1982, 46, 1803. (b) Okuda, T.; Fujiwara, A., Fujiwara, M. Agric. Biol. Chem. 1982, 46, 1811.
3. For the correction of the structure of isonitrin B and the only previous (racemic) synthesis, see: Baldwin, J. E.; Aldous, D. J.; Chan, C.; Harwood, L. M.; O'Neil, I. A.; Peach, J. M. Synlett 1989, 9.
4. For the conversion of isonitrin B to isonitrin A, see: (a) Baldwin, J. E.; O'Neil, I. A. Synlett 1990, 603. For the conversion of an intermediate in the isonitrin B synthesis to trichoviridin, see: (b) Baldwin, J. E.; O'Neil, I.; Russell, A. T. Synlett 1991, 551. (c) Baldwin, J. E.; Adlington, R. M.; O'Neil, I. A.; Russell, A. T.; Smith, M. L. J. Chem. Soc., Chem. Commun. 1996, 41.
5. For the conversion of isonitrin B to isonitrin A, see: (a) Baldwin, J. E.; O'Neil, I. A. Synlett 1990, 603. For the conversion of an intermediate in the isonitrin B synthesis to trichoviridin, see: (b) Baldwin, J. E.; O'Neil, I.; Russell, A. T. Synlett 1991, 551. (c) Baldwin, J. E.; Adlington, R. M.; O'Neil, I. A.; Russell, A. T.; Smith, M. L. J. Chem. Soc., Chem. Commun. 1996, 41.
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17. 3.
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