A collection of benzotriazoles consisting of seven compounds was prepared from the propynyl‐substituted benzolactone 1 and various azides using click chemistry. The lactone 1 was obtained through a short route by direct esterification of the allylbenzoic acid 9 with the alkynol 7 giving the benzoate 2. The homopropargyl alcohol 7 in turn was obtained by opening the epoxide 6 with triisopropylsilyl acetylide. Ring‐closing metathesis of the ester 2 using Grubbs catalyst II followed by removal of the silicon protecting group furnished the lactone 1. Two of the benzotriazoles, 17a and 17b, were also converted into the corresponding phenols to probe the role of the phenolic OH on the biological activity. All nine benzotriazoles showed cytotoxic activity in a L929 mouse fibroblast assay with IC50 values in the low micromolar range. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

A second generation synthesis of the core structure of the macrolactone cruentaren A, a potent FATPase inhibitor, involves the highly functionalized benzoic acid 36 and reaction of an aryl lithium intermediate with the terminal epoxide 30. A methyl benzyl ether in the aryl bromide served as a surrogate for a carboxyl function. Epoxide 30 originated from the aldol product 24. The alkyne of 30 was introduced via opening of an oxetane ring.