Total ssynthesis of (±) thiolactomycin☆

作者: Chia-Lin J. Wang , J.M Salvino

DOI: 10.1016/S0040-4039(01)81574-4

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摘要: Abstract We have completed the first total synthesis of (±)-thiolactomycin by a five-step procedure in 10% overall yield starting from ketoester 6. The key step involves addition dianion 3 to 3-ethoxy-2-methyl-2-propenal. resulting aldehyde 11 was then converted into (±)-thiolactomycin.

参考文章(12)
SATOSHI OMURA, AKIRA NAKAGAWA, RIMIKO IWATA, AKIKO HATANO, Structure of a new antibacterial antibiotic, thiotetromycin. The Journal of Antibiotics. ,vol. 36, pp. 1781- 1782 ,(1983) , 10.7164/ANTIBIOTICS.36.1781
Eberhard Breitmaier, Siegfried Gassenmann, Notiz zur Darstellung von 3-Amino-acroleinen Chemische Berichte. ,vol. 104, pp. 665- 667 ,(1971) , 10.1002/CBER.19711040234
Michael P. Prisbylla, Kunihiko Takabe, James D. White, Stereospecific synthesis of (.+-.)-trisporol B, a prohormone of Blakeslea trispora, and a facile synthesis of (.+-.)-trisporic acids Journal of the American Chemical Society. ,vol. 101, pp. 762- 763 ,(1979) , 10.1021/JA00497A059
SATOHIDE MIYAKAWA, KOJI SUZUKI, TAKAO NOTO, YUSUKE HARADA, HIROSHI OKAZAKI, Thiolactomycin, a new antibiotic. IV. Biological properties and chemotherapeutic activity in mice. The Journal of Antibiotics. ,vol. 35, pp. 411- 419 ,(1982) , 10.7164/ANTIBIOTICS.35.411
HIROSHI SASAKI, HIDEO OISHI, TOSHIAKI HAYASHI, IKUTOSHI MATSUURA, KUNIO ANDO, MIKIO SAWADA, Thiolactomycin, a new antibiotic. II. Structure elucidation. The Journal of Antibiotics. ,vol. 35, pp. 396- 400 ,(1982) , 10.7164/ANTIBIOTICS.35.396
SATOSHI OMURA, YUZURU IWAI, AKIRA NAKAGAWA, RIMIKO IWATA, YOKO TAKAHASHI, HIDEKI SHIMIZU, HARUO TANAKA, Thiotetromycin, a new antibiotic. Taxonomy, production, isolation, and physicochemical and biological properties. The Journal of Antibiotics. ,vol. 36, pp. 109- 114 ,(1983) , 10.7164/ANTIBIOTICS.36.109
ROBERT C. KRUG, TEH FU. YEN, Unsaturated Cyclic Sulfones. I. 3-Bromomethyl-2,5-dihydrothiophene 1,1-Dioxide Journal of Organic Chemistry. ,vol. 21, pp. 1082- 1086 ,(1956) , 10.1021/JO01116A008
E. Earl Royals, Claisen Condensation of Methyl Esters Journal of the American Chemical Society. ,vol. 70, pp. 489- 491 ,(1948) , 10.1021/JA01182A016
HIDEO OISHI, TAKAO NOTO, HIROSHI SASAKI, KOJI SUZUKI, TOSHIAKI HAYASHI, HIROSHI OKAZAKI, KUNIO ANDO, MIKIO SAWADA, THIOLACTOMYCIN, A NEW ANTIBIOTIC The Journal of Antibiotics. ,vol. 35, pp. 391- 395 ,(1982) , 10.7164/ANTIBIOTICS.35.391