Stereocontrolled synthesis of polyfunctionalized cis-decalins from 2-methoxyphenols: total syntheses of (+/-)-eremopetasidione, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilane.
A four-step stereocontrolled synthesis of polyfunctionalized cis-decalins is described, involving oxidation of 2-methoxyphenol, intermolecular Diels-Alder reaction, olefination, and Cope rearrangement. Application of this efficient strategy to the total syntheses of (+/-)-eremopetasidione, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilane was accomplished from creosol and ethyl vinyl ketone via a common intermediate 21.
Hsu
Day-Shin
DS
Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 300.
Hsu
Po-Yi
PY
Lee
Yen-Chun
YC
Liao
Chun-Chen
CC
D003500:Cyclization; D006139:Guaiacol / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C529553:3-angeloyloxyfuranoeremophilane; C529554:3-methacryloyloxyfuranoeremophilane; D009281:Naphthalenes; D012717:Sesquiterpenes; C431987:eremopetasidione; D006139:Guaiacol; C007229:decalin