Asymmetric catalytic synthesis of the proposed structure of trocheliophorolide B.
A concise catalytic asymmetric synthesis of the proposed structure of trocheliophorolide B is reported. The synthetic sequence notably features an asymmetric acetaldehyde alkynylation, a Ru-catalyzed alder-ene reaction, and a Zn-ProPhenol ynone aldol condensation. Comparison with the reported data suggests a misassignment of the natural product structure.
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Barry M
BM
Trost
Adrien
A
Quintard
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D000079:Acetaldehyde / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000480:Alkynes; C579057:trocheliophorolide B; D012428:Ruthenium; D000079:Acetaldehyde; D015032:Zinc; D015107:4-Butyrolactone