Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 15, Pages 4396-4402Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304580
Keywords
alkynes; gold; metathesis; molybdenum; natural products
Categories
Funding
- MPG
- Fonds der Chemischen Industrie
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In an attempt to study the ability of the latest generation of alkyne metathesis catalysts to process sterically hindered substrates, two different routes to the bacterial metabolite kendomycin (1) were explored. Whereas the cyclization of the overcrowded arylalkyne 39 and related substrates turned out to be impractical or even impossible, ring closure of the slightly relaxed diyne 45 was achieved in excellent yield under notably mild conditions with the aid of the molybdenum alkylidyne 2 endowed with triphenylsilanolate ligands. The resulting cycloalkyne 46 was engaged into a gold-catalyzed hydroalkoxylation, which led to benzofuran 47 that had already previously served as a late-stage intermediate en route to 1.
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