Synthesis of Shikimic‐6‐¹³C acid

Abstract

I n s t i t u t Fur M i k r o b i o l o g i e , U n i v e r s i t S t Hohenheim, 7000 S t u t t g a r t 70, Federal Republic o f Germany SUMMARY Shikimic-6-13C acid, 43 t 5% enriched, was synthesized from 91% enriched acetic-2-13C a c i d v i a 91% enriched phosphoenolpyruvic-3-C acid. The l a t t e r intermediate was condensed with erythrose-4-phosphate by a c e l l f r e e e x t r a c t o f E. coli 83-24. 13 Key words: Shikimic acid, carbon-13 NMR Shikimic a c i d (1) i s an important intermediate along t h e aromatic biosynt h e t i c pathway. the i o d i n i n r e p r e s e n t a t i v e o f which we r e c e n t l y studied.

Investigating the reaction mechanism and organocatalytic synthesis of α,α′-dihydroxy ketones

“…[3-13 C]-Li-1 was prepared via the bromination of [3-13 C]-sodium pyruvate (99 atom% 13 C) using neat bromine at 50 °C to give the monobrominated product [3-13 C]-bromopyruvate in 70% yield. 24,25 Then, following a literature protocol to synthesise Li-1, 1 M lithium hydroxide was added slowly to [3-13 C]-bromopyruvate to afford [3-13 C]-Li-1 in 54% yield. 26 Cyclohexanecarboxaldehyde 2a and benzaldehyde 2b were used as representative aliphatic and aromatic aldehydes in the TK biomimetic reaction with [3-13 C]-Li-1 and NMM, affording [1-13 C]-3a and [1-13 C]-3b in 15% and 10% isolated yields, respectively (Scheme 3).…”

“…described. [24][25][26] The pyrrolidine diamines 13a-d were prepared as previously reported. 38,44,45 The cinchona alkaloids 14a-d were commercially available (Sigma-Aldrich).…”