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Synthesis of 10,15-[13C2]-squalene and -DL-squalene oxide

✍ Scribed by Tsutomu Hoshino; Howard J. Williams; Kozo Shishido; A. Ian Scott

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
334 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

[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~/Ο•~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%.

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Synthesis of DL-[2-13C, 15N]aspartic aci
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A synthesis of the title compound from /13Clparaformaldehyde and [15N)ammonium chloride V f 8 ethyl 2-(1 ,3-/2-13Cldithianyl) acetate 3a is described. Ethyl/3-13C13-oxopropanoate derived in sl'tu from 3a was converted by a stepwise Strecker procedure to DL-[ 2-13C,15Nlaspartic acid 7a.