ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 25, Problem 38DSP
Interpretation Introduction

Interpretation:

The structure of alternariolis to be determined on the basis of the information given.

Concept introduction:

Biosynthesis of alternariol takes place in a number of steps involving seven acetate units.

In the first step, an acetyl-CoA reacts with a bicarbonate to form malonyl-CoA. Addition of seven more acetate units forms a fourteen carbon chain.

Cyclization reactions involving two aldol condensations and one lactone ring formation yields the three ring skeletal structure of the final product.

Keto-enol tautomerization in two of these rings converts them to aromatic rings to give the final product, alternariol.

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