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Synthesis of phenolic natural products

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.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.71973
Date January 1984
CreatorsChaly, Thomas.
PublisherMcGill University
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
LanguageEnglish
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Formatapplication/pdf
CoverageDoctor of Philosophy (Department of Chemistry.)
RightsAll items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated.
Relationalephsysno: 000222082, proquestno: AAINL20834, Theses scanned by UMI/ProQuest.

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