Synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral and the kinetic resolution of an allylic silane by a [3 + 2] annulation.
[reaction: see text] The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has been accomplished with this annulation reaction as the key step. Using the pantolactone-derived alpha-keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.
Peng
Zhi-Hui
ZH
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D007700:Kinetics; D009183:Mycotoxins / Q000138:chemical synthesis; D010407:Penicillium / Q000737:chemistry; D006180:Proton-Translocating ATPases / Q000037:antagonists & inhibitors; D012821:Silanes / Q000737:chemistry
D004952:Esters; D005663:Furans; D009183:Mycotoxins; D012821:Silanes; C409727:citreoviral; C005412:pantolactone; D006180:Proton-Translocating ATPases; D015107:4-Butyrolactone