Neoclerodane diterpene

Ortega, A. etal. 1982. Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum (Labiatae). Journal of the Chemical Society Perkins Transactions. 1 1982 2505-2508. 

Salvinorin, a New trans-Neoclerodane Diterpene from Salvia divinorum (Labiatae) J. Chem. Soc. Perkin Trans. 1 2505-2508. 

Salvinorin, isolated from Salvia divinorum has been shown by spectroscopic and X-ray-crystallographic methods to be a tran -neoclerodane diterpene of structure (1). Crystals of compound (1) are orthorhombic, space group P2iP2iP27 with a = 6.368 (2), h = 11.338(3), c = 30.7100 (6) A, and Z = 4. The structure was refined by least-squares to R 0.052 and R 0.056. 

Divinorin C," a New Neoclerodane Diterpene from a Bioactive TLC Fraction of Salvia divinorum... 

Ortega. A 1982 Salvinorin, A New Trans-Neoclerodane Diterpene from... 

The active principle of Salvia divinorum, salvinorin A, is derived from the leaves of the plant. Chemically, salvinorin A is a neoclerodane diterpene, one of a group of nitrogen-containing terpene compounds that have psychotropic properties. Two other such compounds are tetrahydrocannabinol and absinthe. Purified salvinorin A can be obtained from an ether extract of the leaves, which is then concentrated by chromatography and repeated crystallization. 

Epling and Jativa-M) containing the neoclerodane diterpene divinorin A or salvinorin A (Fig. 12.1). It was the first documented non-alkaloidal diterpene hallucinogen. It is inactivated by the gastrointestinal system if orally ingested, and the effect is produced after absorption through the oral mucous. 9... 

VALDES, L.J., CHANG, H.M., VISGER, D.C., KOREEDA, M., Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum., Org. Lett., 2001, 3, 3935-3937. 

Synthesis of Neoclerodane Diterpenes and Their Pharmacological Effects... 

Salvinorin A is a tricyclic trans-cis neoclerodane diterpene containing seven chiral centers. Additionally, 1 contains multiple functional groups, which include four carbonyls at C-l, C-17, C-18, and C-21. Two of the carbonyls are esters off of the C-2 and C-4 positions of the decalin core, and the C-17 carbonyl is part of a 5-lactone ring system. Additionally, 1 contains a furan ring off C-12. Along with the functionality present on 1, C-8 has been shown to undergo epimerization readily in acidic or basic conditions. Despite the molecular complexity, total syntheses of 1 have been accomplished and structural modifications have been completed. This chapter will address total synthetic attempts towards the molecule itself and synthetic methodologies developed and applied to modify the salvinorin A scaffold. 

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