Syntheses of beta-resorcylic acid derivatives, novel potato microtuber inducing substances isolated from Lasiodiplodia theobromae

The syntheses of beta -resorcylic acid derivatives 1 and 2, isolated from f ungus Lasiodiplodia theobromae, and their dimethyl ethers were accomplished . (R)-(-)-1,3-Butanediol was used as a chiral source of the side chain C-6- synthon. The dianion of the benzoic acid moiety was alkylated with C-6-brom ide to give the desired skeleton. Several beta -resorcylic acid derivatives including 1 and 2 were synthesized via hydrogenation, lactonization, demet hylation and esterification. The (R)-configuration of the stereogenic cente r in the side chain was proved by this synthesis. It is confirmed that two phenolic hydroxy groups are required for 1 and 2 to exhibit potato micro-tu ber inducing activity. (C) 2001 Elsevier Science Ltd. All rights reserved.