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Chapter 25: Q20P (page 1144)

Propose a mechanism for the conversion of E isomer of geranyl pyrophosphate to Z isomer.

Short Answer

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The mechanism for the conversion of E isomer of geranyl pyrophosphate to Z isomer.

Step by step solution

01

Undergo in the presence of R-C=O-O-OH

Interconversion of double bond diastereomers can also be brought via epoxidation deoxygenating as shown below.

02

Nucleophilic substitution with tri-phenyl phosphine.

The nucleophilic attack by the phosphorous reagents e.g., tri-phenyl phosphine at oxirane carbon leads to aninversion of configuration and yields a charge separate intermediate.

03

Undergo 180-degree radiation around the C-C bond.

This undergoes elimination which requires 180-degree Celsius radiation around the C-C bond to establish the appropriate geometry.

04

Formation of the Z-isomer.

The bioavailability of Z-isomers is higher than that of all E-isomers during cellular absorption and transport.

Formation of the Z isomer

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