Formal syntheses of heliannuols A and D, allelochemicals from Helianthus annus.
A synthesis of heliannuol A 1 is described involving hydrogenolysis of the cyclopropane fused benzoxepane compound 23 to generate the benzoxocane ring system of 1 and a fragmentation of methyl ether 25 furnished 4-methoxycurcuphenol 29, an advanced intermediate to heliannuol D 4.
Tuhina
Kazi
K
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India.
Bhowmik
Dipal R
DR
Venkateswaran
Ramanathapuram V
RV
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D006368:Helianthus / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D010636:Phenols; D012717:Sesquiterpenes; C476207:heliannuol A; C476206:heliannuol D