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- W2949271479 abstract "An improved synthesis of antimycin A3 was accomplished by a suitable lactonization of 3-O-benzyl or 3-O-isovaleryl derivative (10a or 10b) of (2R, 3R, 4S)-4-(N-benzyloxycarbonyl-L-threonyloxy)-2-butyl-3-hydroxypentanoic acid, which was synthesized by starting from the corresponding 3-O-benzyl or 3-O-isovaleryl derivative (4a or 4b) of methyl 2-C-butyl-2, 5-dideoxy-β-L-arabinofuranoside, respectively. Acid hydrolysis of 4a or 4b followed by reduction with sodium borohydride afforded 3-O-benzyl or 3-O-isovaleryl-1, 3,4-pentanetriol (5a or 5b), respectively. Tritylation of 5a or 5b followed by succesive 4-O-acylation with N-benzyloxycarbonyl-O-t-butyl-L-threonine, detritylation, oxidation with chromium trioxide-acetic acid-pyridine, and de-t-butylation gave the hydroxy ester acid 10a or 10b, respectively. Lactonization of 10a or 10b through its 2-pyridinethiol ester 11a or 11b activated with silver perchlorate afforded the corresponding nine-membered dilactone derivative 12a or 12b in 33 or 13% yield, respec..." @default.
- W2949271479 created "2019-06-27" @default.
- W2949271479 creator A5011667668 @default.
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- W2949271479 date "1979-04-17" @default.
- W2949271479 modified "2023-09-26" @default.
- W2949271479 title "ChemInform Abstract: IMPROVED SYNTHESIS OF ANTIMYCIN A3" @default.
- W2949271479 cites W2167067476 @default.
- W2949271479 doi "https://doi.org/10.1002/chin.197916371" @default.
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