Terpenoids-LV: cyclocostunolides

Kulkarni, G. H. ; Kelkar, G. R. ; Bhattacharyya, S. C. (1964) Terpenoids-LV: cyclocostunolides Tetrahedron, 20 (11). pp. 2639-2645. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)90842-7


α-cyclocostunolide (IV), a product of transannular crystaliaton of costunolide, gives, on treatment with methanol in presence of alkali, (1) α-cyclo-12-methoxydihydrocostunoide (VII) and (2) the corresponding hydroxy acid (VIII). On treatment with ammonia, α-cyclocostunolide is converted to the amide of the hydroxy acid (IX), saponification of which ields VIII. The hydroxy acid (VIII) on catalytic hydrogenation gives the saturated acid (X) which lactonizes to santanolide 'c' on treatment with acid.

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