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Biomimetic rearrangements of simplified labdane diterpenoids

Abstract:

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 cle...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2010.05.052

Authors


George, JH More by this author
McArdle, M More by this author
Baldwin, JE More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Volume:
66
Issue:
33
Pages:
6321-6330
Publication date:
2010-08-14
DOI:
ISSN:
0040-4020
URN:
uuid:7a59647c-7758-4bfc-a40f-eb62f5c1f936
Source identifiers:
67555
Local pid:
pubs:67555

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