Total synthesis of (-)-reveromycin a.
The asymmetric total synthesis of (-)-reveromycin A is described. The key steps involved a Lewis acid catalyzed inverse electron demand hetero-Diels-Alder reaction followed by hydroboration/oxidation to afford the spiroketal core 4 in a highly stereoselective manner and introduction of the C18 hemisuccinate by high-pressure acylation.
School of Chemistry, The University of Melbourne, Victoria 3010, Australia.
Mariana
M
El Sous
Danny
D
Ganame
Peter A
PA
Tregloan
Mark A
MA
Rizzacasa
D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D007202:Indicators and Reagents; D011714:Pyrans; D013141:Spiro Compounds; C409389:reveromycin B; C068098:reveromycin A