Synthesis of the bis-tetrahydropyran core of amphidinol 3.
A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from d-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core.
Crimmins
Michael T
MT
Kenan and Caudill Laboratories of Chemistry, University of North Carolina at Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
Martin
Timothy J
TJ
Martinot
Theodore A
TA
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D004141:Dinoflagellida / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry; D000095722:Amphidinols
D000475:Alkenes; D001688:Biological Products; D008387:Marine Toxins; D035964:Oxocins; D011714:Pyrans; D013644:Tartrates; C438973:amphidinol 3; D000095722:Amphidinols; C029768:tartaric acid
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