Will use Baker's yeast, which can be bought very cheaply from any permarket, in the stereoselective reduction of the "unnatural substrate" ethyl acetoacetate 1. The one functionality in 1 will be converted into an alcohol in the compound ethyl 35- droxybutanoate 2. This useful chiral compound is formed with a high level of enantioselectivity owing this biological reduction.

Will use Baker's yeast, which can be bought very cheaply from any permarket, in the stereoselective reduction of the "unnatural substrate" ethyl acetoacetate 1. The one functionality in 1 will be converted into an alcohol in the compound ethyl 35- droxybutanoate 2. This useful chiral compound is formed with a high level of enantioselectivity owing this biological reduction.

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

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.17P: The following transformation involves a series of four consecutive Heck reactions and the formation...

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Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. You have not studied the Baeyer-Villiger reaction (D to E). The mechanism involves nucleophilic reaction of the peroxyacid with the carbonyl followed by a rearrangement much like that involved in the hydroboration reaction ). Write a mechanism for this reaction.
Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. The tributyltin hydride, Bu3SnH, used in the conversion of (H) to (I) reacts via a radical chain reaction; the first step involves a reaction with a radical initiator to form Bu3Sn?. Suggest a mechanism for the rest of the reaction.
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