Premium
Synthesis of (2′ Z ,6′ E ) and (2′ E ,6′ E )‐[1′‐ 13 C] ubiquinone 3 by means of (2 E ,6 E ) and (2 Z ,6 E )‐[1‐ 13 C] farnesyltrimethyltin reagents
Author(s) -
Sabin Emmanuel,
Boullais Claude
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(1998100)41:10<899::aid-jlcr142>3.0.co;2-j
Subject(s) - chemistry , benzoquinone , carbon 13 nmr , stereochemistry , reagent , medicinal chemistry , organic chemistry
(2 Z ,6 E ) and (2 E ,6 E )‐[1‐ 13 C] farnesates were obtained by a Horner reaction of the geranylacetone with triethyl phosphono [1‐ 13 C] acetate treated with NaH. Reduction of these esters with LiAlH 4 / AlCl 3 gave the corresponding isomeric farnesols which were separated by column chromatography. Each isomer was brominated with PBr 3 to provide the corresponding bromo derivatives which were then reacted with Me 3 SnLi to afford the farnesyltrimethyltins. The latter were coupled with 2,3‐dimethoxy‐5‐methyl‐1,4‐benzoquinone in the presence of BF 3 .OEt 2 followed by oxidation with Ag 2 O to give rise to (2′ Z ,6′ E ) and (2′ E ,6′ E )‐5,6‐dimethoxy‐2‐farnesyl‐3‐methyl‐[1′‐ 13 C] 1,4‐benzoquinone.Copyright © 1998 John Wiley & Sons, Ltd.