The following stereospecific synthesis is part of the scheme used by E. J. Corey of Har- vard University in the synthesis of erythronolide B, the precursor of the erythromycin antibiotics. In this remarkably simple set of reactions, the relative configurations of five chiral centers are established. OH 1. ВН, THF CrOg, H,SO4 CH;ONa 2. Н,О», NaOH acetone 2,4,6-Trimethyl- phenol HO COOH A B C Br Br Brg, H,O КОН Brg, H,O KBr THE KBr СООН E F
The following stereospecific synthesis is part of the scheme used by E. J. Corey of Har- vard University in the synthesis of erythronolide B, the precursor of the erythromycin antibiotics. In this remarkably simple set of reactions, the relative configurations of five chiral centers are established. OH 1. ВН, THF CrOg, H,SO4 CH;ONa 2. Н,О», NaOH acetone 2,4,6-Trimethyl- phenol HO COOH A B C Br Br Brg, H,O КОН Brg, H,O KBr THE KBr СООН E F
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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Question
Propose a mechanism for the conversion of 2,4,6-trimethylphenol to compound A.

Transcribed Image Text:The following stereospecific synthesis is part of the scheme used by E. J. Corey of Har-
vard University in the synthesis of erythronolide B, the precursor of the erythromycin
antibiotics. In this remarkably simple set of reactions, the relative configurations of five
chiral centers are established.
OH
1. ВН, THF
CrOg, H,SO4
CH;ONa
2. Н,О», NaOH
acetone
2,4,6-Trimethyl-
phenol
HO
COOH
A
B
C
Br
Br
Brg, H,O
КОН
Brg, H,O
KBr
THE
KBr
СООН
E
F
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