Total Synthesis of Chiricanine A, Arahypin-1, trans-Arachidin-2, trans-Arachidin-3, and Arahypin-5 from Peanut Seeds

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.