Journal
TETRAHEDRON
Volume 66, Issue 33, Pages 6321-6330Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.05.052
Keywords
Biomimetic synthesis; Labdanes; Clerodanes
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Simplified ethyl-substituted labdane diterpenoids 14 and 19 have been synthesised from (+)-sclareolide (18). Biomimetic rearrangements of these compounds, involving stereospecific 1,2-alkyl and hydride shifts, have been carried out by treatment with a variety of Lewis and protic acids. Halimane compounds, such as 34 and simple dehydration products such as 3, 32 and 33 have been formed either selectively or as mixtures depending on the reaction conditions. However, further rearrangement to clerodane products such as 1 and 2 was not observed, indicating a high degree of enzymatic control for the in vivo formation of these natural products. (C) 2010 Elsevier Ltd. All rights reserved.
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