Total synthesis of amphidinolide E.
A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF3.Et2O promoted [3+2] annulation reaction between aldehyde 3 and allylsilane 4 to afford substituted tetrahydrofuran 2.
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Porino
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Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
Roush
William R
WR
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D004951:Esterification; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry; D000097442:Amphidinolides
D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D012821:Silanes; C452448:amphidinolide E; D000097442:Amphidinolides