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Erowid References Database

Scheerer JR, Lawrence JF, Wang GC, Evans DA. 
“Asymmetric Synthesis of Salvinorin A, A Potent K Opioid Receptor Agonist”. 
JACS. 2007 may 18;.
Abstract
The neoclerodane diterpene salvinorin A (1) was isolated in 1982 from the rare mint SalVia diVinorum, indigenous to Oaxaca, Mexico.1 Recent efforts established salvinorin A as a potent and selective ! opioid receptor agonist, the only non-alkaloid psychoactive substance, and the most potent naturally occurring hallucinogen.2 As a result of its therapeutic potential, renewed isolation efforts have discovered a number of related salvinorin congeners,3 and a number of analogues of 1 have been prepared by semisynthesis to probe the pharmacophore and mode of binding.4 This communication describes the first synthesis of this natural product.

Construction of the tricyclic salvinorin core is predicated on the proposed transannular5 Michael reaction cascade6 of bisenone macrocycle 3 (Scheme 1). Conformational analysis7 of 3 leads to a prediction wherein the resident stereocenters at C2, C4, and C12 should mutually reinforce the desired stereochemical course of the reaction. This plan permits the convergent assembly of vinyl iodide 4 and aldehyde 5, which can be prepared through established methods.
Notes # : salvia salvinorin synthesis
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