Synthesis of amphidinolide E C10-C26 fragment.
The key C10-C26 fragment in a total synthesis of (-)-amphidinolide E has been prepared from an oxolane-containing C10-C17 segment (9, derived from L-glutamic acid) via a Julia-Kocienski reaction with aldehyde 3, followed by a Sharpless AD to obtain the desired diol. The C22-C26 fragment was installed by means of an efficient Suzuki-Molander coupling, with an organotrifluoroborate reagent (4, arising from a cross-metathesis reaction between a vinylboronate and 2-methyl-1,4-pentadiene).
Esteban
Jorge
J
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Av. Diagonal 647, 08028 Barcelona, Catalonia, Spain.
Costa
Anna M
AM
Vilarrasa
Jaume
J
D000468:Alkalies / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D000097442:Amphidinolides
D000468:Alkalies; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002244:Carbon; D003432:Cross-Linking Reagents; C452448:amphidinolide E; D000097442:Amphidinolides