First total syntheses of (+/-)-annuionone B and (+/-)-tanarifuranonol.
The intramolecular Diels-Alder reaction of o-quinol allyl ether was accomplished and subsequently applied to the first total syntheses of natural products annuionone B (1) and both the proposed and revised structure of tanarifuranonol, 4 and 17.
Shiao
Hui-Yi
HY
Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan.
Hsieh
Hsing-Pang
HP
Liao
Chun-Chen
CC
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006368:Helianthus / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D013729:Terpenes; C527915:annuionone B; C527916:tanarifuranonol