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Synthesis of 10,15‐[ 13 C 2 ]‐squalene and ‐DL‐squalene oxide
Author(s) -
Hoshino Tsutomu,
Williams Howard J.,
Shishido Kozo,
Ian Scott A.
Publication year - 1990
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/jlcr.2580281108
Subject(s) - chemistry , squalene , decarboxylation , bromide , hydrolysis , oxide , aqueous solution , yield (engineering) , ketone , organic chemistry , medicinal chemistry , nuclear chemistry , catalysis , materials science , metallurgy
[3‐ 13 C]‐Ethyl farnesoate was prepared by alkylating 3‐ 13 C‐ethyl acetoacetate with geranyl bromide, followed by hydrolysis, decarboxylation and treatment with the anion of triethyl phosphonoacetate. The ester was reduced with LAH, brominated with CBr 4 /ϕ 3 P, and the farnesyl bromide coupled with CuI/Li‐pyrrolidine to produce [10,15‐ 13 C 2 ]‐squalene. Epoxidation was effected by treatment with NBS in aqueous THF, followed by K 2 CO 3 ‐mediated HBr elimination. The overall yield of DL‐10,15‐[ 13 C 2 ]‐squalene‐2,3‐oxide was 1.6%.