An asymmetric total synthesis of (+)-pentalenene

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A stereoselective total synthesis of (+)-pentalenene was achieved through the tandem cycloaddition reaction of the allenyl diazo substrate prepared from (+)-citronellal. The initial intramolecular [2+3] cycloaddition reaction between the diazo functionality and the allenyl group produced the trimethylenemethane (TMM) intermediate after immediate loss of nitrogen molecule from the cycloaddition intermediate. Subsequent [2+3] cycloaddition of the TMM with olefin produced the angularly fused triquinane structure stereoselectively. (C) 2013 Elsevier Ltd. All rights reserved.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Issue Date
2013-09
Language
English
Article Type
Article
Keywords

ANGULAR TRIQUINANES; (+/-)-DEOXYPENTALENIC ACID; TRIMETHYLENEMETHANE DIYLS; (+/-)-PENTALENIC ACID; RADICAL CYCLIZATION; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; IDEAL SYNTHESIS; PENTALENENE; CYCLOADDITION

Citation

TETRAHEDRON, v.69, no.36, pp.7810 - 7816

ISSN
0040-4020
DOI
10.1016/j.tet.2013.05.095
URI
http://hdl.handle.net/10203/254496
Appears in Collection
CH-Journal Papers(저널논문)
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