Studies on the synthesis of the mycalamides: Stereocontrolled synthesis of a model N-glycosylpederamide via a stereoselective aldol reaction

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2064-2065

  Roush, William R ^a,b   Pfeifer, Lance A ^a   Marron, Thomas G ^a  

^a INDIANA UNIVERSITY   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; MYCALAMIDE A; MYCALAMIDE B; N GLYCOSYLPERAMIDE; PEDERAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; MODEL; STEREOCHEMISTRY;

EID: 0032478579     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980023k     Document Type: Article

References (22)

1. Total syntheses of mycalamides A and B: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242. (b) Nakata, T.; Fukui, H.; Nakagawa, T.; Matsukura, H. Heterocycles 1996, 42, 159. (c) Synthesis of 18-O-methyl mycalamide B: Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797.
2. Total syntheses of mycalamides A and B: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242. (b) Nakata, T.; Fukui, H.; Nakagawa, T.; Matsukura, H. Heterocycles 1996, 42, 159. (c) Synthesis of 18-O-methyl mycalamide B: Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797.
3. Total syntheses of mycalamides A and B: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242. (b) Nakata, T.; Fukui, H.; Nakagawa, T.; Matsukura, H. Heterocycles 1996, 42, 159. (c) Synthesis of 18-O-methyl mycalamide B: Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797.
4. Other synthetic studies on the mycalamides: (a) Hoffmann, R. W.; Schlapbach, A. Tetrahedron Lett. 1993, 34, 7903. (b) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346.
5. Other synthetic studies on the mycalamides: (a) Hoffmann, R. W.; Schlapbach, A. Tetrahedron Lett. 1993, 34, 7903. (b) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346.
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22. Leading references to all previous syntheses of pederic acid and pederamide derivatives are provided in ref 9.