Total Synthesis of Everninomicin 13,384-1—Part 2: Synthesis of the FGHA2 Fragment

1'-disaccharide and the two orthoesters of this target molecule were introduced by new methodologies using a tin acetal and 1,2-phenylseleno migrations. The reaction sequence also relies on stereoselective glycosidations and subtle manipulations of protecting groups. In addition to the introduction of new synthetic methodologies, this total synthesis should allow the preparation of combinatorial libraries of semisynthetic analogues of this highly promising antibiotic for biological screening purposes. -->
ISSN: 1521-3773
1433-7851
DOI: 10.1002/(sici)1521-3773(19991115)38:22<3340::aid-anie3340>3.0.co;2-2
Přístupová URL adresa: https://explore.openaire.eu/search/publication?articleId=doi_________::5314aa9fbfff966b4a8ca1cdd6b658ce
https://doi.org/10.1002/(sici)1521-3773(19991115)38:22<3340::aid-anie3340>3.0.co;2-2
Rights: CLOSED
Přírůstkové číslo: edsair.doi...........5314aa9fbfff966b4a8ca1cdd6b658ce
Autor: Kyriacos C. Nicolaou, Olivier Baudoin, Hideo Suzuki, Konstantina C. Fylaktakidou, Rosa Maria Rodríguez, Helen J. Mitchell
Rok vydání: 1999
Předmět:
Zdroj: Angewandte Chemie International Edition. 38:3340-3345
ISSN: 1521-3773
1433-7851
DOI: 10.1002/(sici)1521-3773(19991115)38:22<3340::aid-anie3340>3.0.co;2-2
Popis: The powerful antibiotic everninomicin 13,384-1 (1, Ziracin) has been prepared for the first time through a total synthesis. The 1-->1'-disaccharide and the two orthoesters of this target molecule were introduced by new methodologies using a tin acetal and 1,2-phenylseleno migrations. The reaction sequence also relies on stereoselective glycosidations and subtle manipulations of protecting groups. In addition to the introduction of new synthetic methodologies, this total synthesis should allow the preparation of combinatorial libraries of semisynthetic analogues of this highly promising antibiotic for biological screening purposes.
Databáze: OpenAIRE
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