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- Title
Synthese des Makrolid-Antibiotikums (−)-A26771B mit Photolactonisierung als Schlüsselreaktion und Computersimulation als effektive Optimierungshilfe.
- Authors
Quinkert, Gerhard; Küber, Frank; Knauf, Wolfgang; Wacker, Manfred; Koch, Uwe; Becker, Heinrich; Nestler, Hans Peter; Dürner, Gerd; Zimmermann, Gottfried; Bats, Jan W.; Egert, Ernst
- Abstract
Synthesis of the Macrolide Antibiotic (−)-A2677IB Using Photolactonization as a Key Reaction and Computer Simulation as an Effective Aid in Optimization The title compound has been synthesized in a sequence of 21 steps starting from phenol. The cyclic skeleton has been built up in the earlier part of the synthesis by photolactonization. This reaction supplies C(6), with a functionality, not present in the target structure, but useful for oxygenation at C(4) and generation of the stereogenic center C(5). The Barton/ McCombie reaction provides a product deoxygenated at C(6), but only after an adjacent oxirane ring has been opened at the cost of an increase in the number of overall steps. X-Ray structural information and computational modelling of appropriate molecules proved to be essential to selection of optimal conditions for various transformations.
- Publication
Helvetica Chimica Acta, 1991, Vol 74, Issue 8, p1853
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19910740828