title: Total synthesis of chiricanine A, arahypin-1, trans-arachidin-2, trans-arachidin-3, and arahypin-5 from peanut seeds.
abstract: The first and efficient syntheses of the naturally occurring prenylated stilbenes chiricanine A (2), arahypin-1 (3), trans-arachidin-2 (4), trans-arachidin-3 (5), and arahypin-5 (6) are described. Syntheses of 2 and 3 were accomplished by either a convergent sequence or a one-step reaction starting from pinosylvin. Syntheses of 4, 5, and 6 were achieved from (E)-3,5-bis-methoxymethyl-4'-triisopropylsilyloxystilbene obtained by a Horner-Wadsworth-Emmons reaction between a benzaldehyde possessing bis-methoxymethyl ether groups and a benzyl phosphonate with a triisopropylsilyloxy group.
authors.affiliation: School of Chemical Engineering and Technology, Yeungnam University, Gyeongsan 712-749, Korea.
authors.forename: Byung Ho
authors.initials: BH
authors.lastname: Park
authors.forename: Hee Jin
authors.initials: HJ
authors.lastname: Lee
authors.forename: Yong Rok
authors.initials: YR
authors.lastname: Lee
mesh_terms: D010367:Arachis / Q000737:chemistry; D045782:Hemiterpenes; D015394:Molecular Structure; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D045782:Hemiterpenes; D013267:Stilbenes; C553171:arachidin-3; C559010:arahypin-1; C559012:arahypin-5; C559008:chiricanine A; C559009:trans-arachidin-2; C559011:trans-arachidin-3