Tandem intramolecular Michael-aldol reaction as a tool for the construction of the C-ring of hexacyclinic acid.
[reaction: see text] The tandem intramolecular Michael-aldol reaction was studied as a tool for the construction of the C-ring of hexacyclinic acid. By changing the reaction conditions it was possible to selectively obtain either the kinetic or the thermodynamic product. Retro-aldol reaction and subsequent epimerization provides four individual cyclopentane derivatives that can be incorporated as building blocks in natural product syntheses.
Stelmakh
Andriy
A
Institute of Organic Chemistry, University of Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
Stellfeld
Timo
T
Kalesse
Markus
M
D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry
D006576:Heterocyclic Compounds, 4 or More Rings; D018942:Macrolides; C502347:hexacyclinic acid