Synergistic factors ensue high expediency in the synthesis of menaquinone [K2] analogue MK-6: Application to access an efficient one-pot protocol to MK-9

Nanaji Yerramsetti, Lavanya Dampanaboina, Venugopal Mendu, Satyanarayana Battula

Research output: Contribution to journalArticlepeer-review

Abstract

Here we report a practical and efficient method for the synthesis of menaquinone vitamin (K2) analog MK-6 in all trans forms through “1 + 5 convergent synthetic approach” of pentaprenyl chloride with monoprenyl menadione derivative. In the synergistic factors, less efficient leaving group/more efficient nucleophile (Cl) in the substrate makes it more prominent reaction by eliminating all Sn2’ side reaction products. Further, the addition of acetic acid in the last step (desulfonation) of reaction sequence removes the limitations of the reactions in terms of cyclized side product (multiple reactions of pentaprenyl alcohol with Et3B), byproduct (Et3B, incendiary compound) formations and their interruption in the tricky purification processes. The utility of this method was further extended to find an efficient one-pot synthesis to MK-9 to the gram scale synthesis. This approach is economical and efficient and avoids the awkward chromatographic separation processes.

Original languageEnglish
Article number131696
JournalTetrahedron
Volume76
Issue number49
DOIs
StatePublished - Dec 4 2020

Keywords

  • AcOH quenching
  • Chlorine nucleophile
  • MK-9
  • Vitamin K MK-6

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