Chlorocatechelin A was isolated from a bacterial culture, but it had to be synthesized in the laboratory in order to obtain enough pure material for the study of its antimicrobial activity. Shown below is the first step of a 15-step synthesis of chlorocatechelin A, starting with ortho-vanillin. Propose a plausible mechanism for this reaction (pyridine is a base that can deprotonate the acidic phenol proton in ortho- vanillin to some extent). Include lone pairs and charges in your answer. NH2 но он о 14 steps MoO. Pyridine OH но. OH ortho-Vanilin N. H. Chlorocatocholin A

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.58P
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PLEASE SHOW STEP BY STEP! ALSO PLEASE INCLUDE ALL ELECTRON LONE PAIRS AND CHARGES FOR STRUCTURES IF NECESSARY!

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Chlorocatechelin A was isolated from a bacterial culture, but it had to be synthesized in the laboratory
in order to obtain enough pure material for the study of its antimicrobial activity. Shown below is the
first step of a 15-step synthesis of chlorocatechelin A, starting with ortho-vanillin. Propose a plausible
mechanism for this reaction (pyridine is a base that can deprotonate the acidic phenol proton in ortho-
vanillin to some extent). Include lone pairs and charges in your answer.
CI.
NH2
HO
он
14 steps
OH
Meo
Meo
H.
Pyridine
OH
но
N.
ortho-Vanilin
N.
HO.
N.
H.
Chlorocatechelin A
OH
Transcribed Image Text:Chlorocatechelin A was isolated from a bacterial culture, but it had to be synthesized in the laboratory in order to obtain enough pure material for the study of its antimicrobial activity. Shown below is the first step of a 15-step synthesis of chlorocatechelin A, starting with ortho-vanillin. Propose a plausible mechanism for this reaction (pyridine is a base that can deprotonate the acidic phenol proton in ortho- vanillin to some extent). Include lone pairs and charges in your answer. CI. NH2 HO он 14 steps OH Meo Meo H. Pyridine OH но N. ortho-Vanilin N. HO. N. H. Chlorocatechelin A OH
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