Synthesis of racemic frenolicin B and 5-epi-frenolicin B via intramolecular palladium-catalyzed aryloxycarbonylation

Synthesis

Volumn , Issue 5, 1999, Pages 821-828

  Contant, Pierre ^a   Haess, Martin ^b   Riegl, Johann ^a   Scalone, Michelangelo ^b   Visnick, Mike ^c,d  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

^c HOFFMANN LA ROCHE INC   (United States)

^d PFIZER INC   (United States)

Author keywords

Palladium catalyzed aryloxycarbonylation; rac 5 epi frenolicin B; rac deoxyfrenolicin; rac frenolicin B

Indexed keywords

DEOXYFRENOLICIN; FRENOLICIN B; GAMMA LACTONE DERIVATIVE; PALLADIUM; PYRANONAPHTHOQUINONE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CATALYSIS; STEREOCHEMISTRY; STREPTOMYCES; SYNTHESIS; X RAY ANALYSIS;

EID: 0032943266     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3482     Document Type: Article

References (35)

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17. To the best of our knowledge the crystal structure of only one other member of pyranonaphthoquinones, i.e. kalafungin, has been determined: Duchamp, D.J., The crystal and molecular Structure of kalafungin, Amer. Cryst. Assoc. Abstr. Papers, Summer Meeting. 82, 1968, cited in Hoeksema, H.; Krueger, W.C., J. Antibiotics 1976, 29, 704. However, no data could be found in accessible data bases. C. Hubschwerlen, F. Hoffmann-La Roche AG Basel, has completed a synthesis of frenolicin B confirming the absolute stereochemistry of this natural product. G. Moine, F. Hoffmann-La Roche AG Basel, has synthesized the (4aR, 10aR)-dihydroxy analogue of deoxyfrenolicin as its (-)-menthol ester and determined the absolute stereochemistry by X-ray analysis. This work has not been published externally to date.
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