Total synthesis of macrosphelides A, B, and E: first application of ring-closing metathesis for macrosphelide synthesis.
A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.
Kawaguchi
Takanori
T
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0194, Japan.
Funamori
Nobutaka
N
Matsuya
Yuji
Y
Nemoto
Hideo
H
D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D006571:Heterocyclic Compounds; D018942:Macrolides; C097798:macrosphelide A; C097799:macrosphelide B; C483571:macrosphelide E