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Applications of the Dotz benzannulation reaction in natural product synthesis

section I of this thesis contains a brief resume of the recent literature reports concerning the chemistry of Fischer Carbene Complexes. The latter part of the review discusses the mechanism of the Dotz benzannulation reaction. section II describes the author's own work, relating to the use of Fischer Carbene Complexes in organic synthesis. The main objectives of the research undertaken were to investigate the synthetic potential of the Shapiro/Dotz benzannulation sequence in natural product synthesis. Initial model studies involved the synthesis of 4-ethoxy-3-methoxy-2- (1' -methylethyl)- 5,6,7,8-tetrahydronaphth-l-ol and 3-methoxy-2-(1'- methylethyl)-5,6,7,8-tetrahydro-l,4-naphthoquinone from pentacarbonyl( ethoxycyclohex-l-enecarbene)-chromium (0) and 1- methoxy-3-methylbut-l-yne.pentacarbonyl(ethoxycyclohex-l-ene carbene)-chromium (0) was prepared by Shapiro chemistry from cyclohexanone 2,4,6-triisopropylbenzenesulphonyl hydrazone.

Identiferoai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:629435
Date January 1991
CreatorsKing, John D.
PublisherUniversity of Manchester
Source SetsEthos UK
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation

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