Helvetica Chimica Acta p. 734 - 744 (1992)
Update date:2022-07-29
Topics:
Wirth, Dieter
Fischer-Lui, Iris
Boland, Wilhelm
Icheln, Detlef
Runge, Thorsten
et al.
Unusual and novel C11H16 olefins with (E)- or (E,E)-configuration instead of the previously known (Z)- or (E,Z)-configuration at the double bond(s) within the longer side chain are the main products of the Australian phaeophyte Dictyopteris acrostichoides.This configuration anomaly refers to all four series of alicyclic C11H16 hydrocarbons, namely the disubstituted cyclopentenes and cyclopropanes, as well as the monosubstituted cycloheptadienes and cyclopentenes.Chiral compounds within the above series have the same absolute configuration.The two (cyclopent-3-enyl)hexa-1,3-dienes 11 and 13 are found for the first time.The absolute configuration and optical purity of the hydrocarbons are determined by gas chromatography on modified cyclodextrins as chiral stationary phases.The synthesis of chiral references via lipase-catalyzed resolutions is described.
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Doi:10.1080/00397919208021344
(1992)Doi:10.1021/acschemneuro.1c00079
(2021)Doi:10.1039/j39660000971
(1966)Doi:10.1021/ja402193f
(2013)Doi:10.1002/ejoc.201201290
(2013)Doi:10.1016/j.tet.2013.04.006
(2013)