Elsevier

Tetrahedron Letters

Volume 41, Issue 4, 22 January 2000, Pages 465-469
Tetrahedron Letters

Studies toward the total synthesis of Sch 202596, an antagonist of the galanin receptor subtype GalR1: synthesis of geodin, the spirocoumaranone subunit of Sch 202596

https://doi.org/10.1016/S0040-4039(99)02005-5Get rights and content

Abstract

An efficient synthesis of (±)-geodin [(±)-2] corresponding to the spirocoumaranone subunit of Sch 202596 (1) was accomplished in a convergent manner by utilizing coupling reaction of the aryl aldehyde 5 with the aryl bromide 6 and oxidative spirocyclization of the benzophenone 4 as the key steps. The aromatic segments 5 and 6 were prepared from commercially available methyl 3,5-dihydroxybenzoate (7) and 5-methylresorcinol (8), respectively.

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