Synthesis of phenolic natural products

• Main Author: Chaly, Thomas.
• Format: Others
• Language: en
• Published: McGill University 1984
• Subjects: Phenols.; Carbonyl compounds.
• Online Access: http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=71973

A new method for the acetalization of carbonyl compounds using chlorotrimethylsilane under mild conditions is described. Carbonyl compounds are acetalized by ethylene glycol with chlorotrimethylsilane. === Two isomeric methyl olivetolates were synthesised by the condensation of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene with the corresponding electrophilic components. This reaction has clearly indicated the discriminative behaviour of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene towards different electrophilic sites thus leading to regio-selectivity. === A new method for the synthesis of olivetol is described. This method provides a shorter route to olivetol from acyclic precursors. === A new synthesis of (DELTA)('1)-tetrahydrocannabinol is described. The synthesis is patterned after biogenetic considerations. === A new method for the synthesis of poly (beta)-carbonyl compounds using diketene and enol silyl ethers is described. === The possibility of synthesising gossypol by the cyclo-aromatization procedure was investigated.