Total synthesis of pradimicinone, the common aglycon of the pradimicin-benanomicin antibiotics

Angewandte Chemie - International Edition

Volumn 38, Issue 9, 1999, Pages 1229-1232

  Kitamura, Mitsuru ^a   Ohmori, Ken ^a   Kawase, Toshihisa ^a   Suzuki, Keisuke ^a  

^a Tokyo Institute of Technology ^*  (Japan)

Author keywords

Antibiotics; Antifungal agents; Benanomicin; Pradimicin; Total synthesis

Indexed keywords

ANTIBIOTIC AGENT; BENANOMICIN A; NATURAL PRODUCT; PRADIMICIN A; PRADIMICIN C; PRADIMICINONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0033519228     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B     Document Type: Article

References (24)

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20. Clearly, this stage is a good opportunity to asymmetrize the material by employing Bringmann's asymmetric ring opening reaction: G. Bringmann, R. Walter, R. Weirich, Tetrahedron 1993, 49, 7891-7902.
21. That the diastereomer 20a has the requisite chirality (M) was judged by the CD spectra of the two enantiomers of 18, derived from 20a and 20b, respectively.
22. Determined by HPLC analysis (DAICEL CHIRALCEL OD-H (25 cm, 0.46 cm diameter), hexane/iPrOH 9/1).
23. 1H NMR measurement on a mixed sample of synthetic and authentic materials fully coincided.
24. 1H NMR spectra were observed arising from the 5,6-bis-epimer (relative to the D-alanine moiety).