Chemistry of ayurvedic crude drugs - VII guggulu (resin from Commiphora mukul) -6: Absolute stereochemistry of guggultetrols

Kumar, Vijay ; Sukh Dev, (1987) Chemistry of ayurvedic crude drugs - VII guggulu (resin from Commiphora mukul) -6: Absolute stereochemistry of guggultetrols Tetrahedron, 43 (24). pp. 5933-5948. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)87799-1

Abstract

With a view to elucidating the stereochemistry of quqqultetrols, components of saponified Commiphora mukul resin, D-lyxo-, L-ribo-, and L-xylo-octadecane-1,2,3,4-tetrols have been synthesised by two different routes. One method starts with D-glyceraldehyde, while the second route is based on the appropriate pentose. The absolute configuration of the natural product guggultetrol-18, has been deduced as D-xylo (2S, 3S, 4R-configuration) by direct comparison with synthetic compounds. This work also serves to establish the chirality of guggultetrol-20.

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