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- W1963717084 abstract "Abstract Giffordene (=(2 Z ,4 Z ,6 E ,8 Z )‐2,4,6,8‐undecatetraene; 9f ) and five steroisomers are new C 11 H 16 hydrocarbons from the marine brown alga Giffordia mitchellae . Their synthesis is based on non‐stereoselective Wittig reactions of ( E )‐2‐alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting ( E/Z )‐pairs. The uniform enynes (>98% purity) are then stereospecifically reduced to ( Z )‐alkenes with Zn(Cu/Ag) in aq. MeOH at r.t. 13 C‐ and 1 H‐NMR data of the new tetraenes are presented. Biosynthetically, giffordene ( 9f ) originates from dodeca‐3,6,9‐trienoic acid via an unstable (3 Z ,5 Z ,8 Z )‐1,3,5,8,‐undecatetraene followed by a thermally allowed antarafacial 1,7‐sigmatropic hydrogen shift to the (2 Z ,4 Z ,6 E ,8 Z )‐isomer 9f ." @default.
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- W1963717084 date "1987-07-08" @default.
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- W1963717084 title "Sterospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown AlgaGiffordia mitchellae. Part IV." @default.
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- W1963717084 doi "https://doi.org/10.1002/hlca.19870700415" @default.
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