Synthesis of the core structure of cruentaren A.
The core structure of the macrolactone cruentaren A (1) was prepared via a ring-closing alkyne metathesis reaction. The corresponding ester 33 was constructed from the benzoic acid derivative 14 and the diol 30. As a key step in the synthesis of acid 14, an aldol reaction resulted in the required anti-OH/Me pattern. The anti-configuration in the stereotetrad of diol 30 was established by a Marshall reaction. [reaction: see text].
Vintonyak
Viktor V
VV
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
Maier
Martin E
ME
D000480:Alkynes / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis*; D019817:Benzoic Acid / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism
D000480:Alkynes; D000935:Antifungal Agents; D004952:Esters; D007202:Indicators and Reagents; D018942:Macrolides; C516694:cruentaren A; D019817:Benzoic Acid; D008094:Lithium