1460-97-5Relevant articles and documents
Lessons from 1,3-Hydride Shifts in Sesquiterpene Cyclizations
Rinkel, Jan,Rabe, Patrick,Garbeva, Paolina,Dickschat, Jeroen S.
, p. 13593 - 13596 (2016)
Stereospecifically labelled precursors were subjected to conversion by seven bacterial sesquiterpene cyclases to investigate the stereochemistry of their initial 1,10-cyclisation-1,3-hydride shift cascades. Enzymes with products of known absolute configuration showed a coherent stereochemical course, except for (?)-α-amorphene synthase, for which the obtained results are better explained by an initial 1,6-cyclisation. The link between the absolute configuration of the product and the stereochemical course of the 1,3-hydride shifts enabled assignment of the absolute configurations of three enzyme products, which were confirmed independently through the absolute configuration of the common byproduct germacrene D-4-ol.
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Kalsi,P.S. et al.
, p. 1073 - 1078 (1963)
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Stereostructure of vetidiol, a new antipodal sesquiterpene diol from vetiver oil; A novel role of biological activity to predict the position and stereochemistry of one of the hydroxyl group
Kalsi,Talwar
, p. 2985 - 2988 (2007/10/02)
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