An efficient synthesis of antibiotic (-)-A26771B

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 612-615

  Kobayashi, Yuichi ^a   Okui, Hiroki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

A 26771 B; ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CYCLIZATION; DRUG STRUCTURE; JAPAN; SYNTHESIS;

ANTI-BACTERIAL AGENTS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0034723231     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991282s     Document Type: Article

References (26)

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19. 3 The synthesis, however, suffers from low yields in some steps involved. Moreover, selective hydrolysis of the methyl succinate part to obtain acid 1 is not described.
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21. 3) followed by ozonolysis. See the Experimental Section for details.
22. 1H NMR spectrum of the MTPA ester of (S)-6 with that of rac-6.
23. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
24. A mixture of 14 and the epimer at C(5) was synthesized by the method of Scheme 1 using racemic alcohol rac-6 as the C(1)-C(13) part.
25. 1H NMR spectrum of the epimer: δ 4.36 (t, J = 6 Hz, 1 H), 6.75 (d, J = 16 Hz, 1 H), 7.24 (d, J = 16 Hz, 1 H).
26. The synthesis was achieved with 12 steps in 6.3% overall yield.