Organic Letters 2006-10-12

The first total synthesis of (-) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization.

Isamu Shiina, Takaaki Kikuchi, Akane Sasaki

Index: Org. Lett. 8 , 4955, (2006)

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Abstract

[structure: see text] An effective method for the total synthesis of 2-hydroxy-24-oxooctacosanolide, a defensive salivary secretion of the African termite Pseudacanthotermes spiniger, has been developed. The key lactonization to form a 29-membered ring lactone core is performed using 2-methyl-6-nitrobenzoic anhydride with a catalytic amount of 4-(dimethylamino)pyridine N-oxide.