Synthesis of the C1-C52 fragment of amphidinol 3, featuring a beta-alkoxy alkyllithium addition reaction.
An advanced intermediate for the synthesis of amphidinol 3 has been prepared. A cross-metathesis reaction was used to couple the C1-C12 and C13-C26 segments. An unusual beta-alkoxy alkyllithium reagent was generated from this segment and added to a Weinreb amide to assemble the C1-C52 section of amphidinol 3. These compounds represent some of the most advanced intermediates reported to date for the synthesis of amphidinol 3.
Huckins
John R
JR
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697-2025, USA.
de Vicente
Javier
J
Rychnovsky
Scott D
SD
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D000095722:Amphidinols
D000447:Aldehydes; D000475:Alkenes; D000577:Amides; D018020:Lithium Compounds; D011714:Pyrans; C438973:amphidinol 3; D000095722:Amphidinols