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Can I read Highly Functionalized Bicyclo[3.2.1]octane Derivatives from Readily Available 2′-Alkoxytricyclo[3.2.1.02,7]octanes: Building Blocks for Terpenes, Part I on EtoBox?
Highly Functionalized Bicyclo[3.2.1]octane Derivatives from Readily Available 2′-Alkoxytricyclo[3.2.1.02,7]octanes: Building Blocks for Terpenes, Part I by Armin de Meijere; Lazaros Hadjiarapoglou; Mathias Noltemeyer; Hans-Jürgen Gutke; Iris Klein; Dietrich Spitzner is a Chemistry article available to read on EtoBox.
What is Highly Functionalized Bicyclo[3.2.1]octane Derivatives from Readily Available 2′-Alkoxytricyclo[3.2.1.02,7]octanes: Building Blocks for Terpenes, Part I about?
2Ј-Alkoxytricyclo[3.2.1.0 2,7 ]octanes 4-R are obtained in good give chelation-stabilized cyclopropyllithium derivatives 6-Me, which react with electrophiles to yield the 7Ј-substituted to excellent yields from methyl 2-chloro-2-cyclopropylideneacetate (3) and the dienolates derived from the 3-alkoxycyc-tricyclo[3.2.1.0 2,7 ]octanes 4f؊i-Me (61Ϫ66%). By acidic workup of such reaction mixtures, or subsequent treatment lohex-2-enones 1-R and 2-R, by a cascade of two consecutive Michael additions and a γ-elimination. Compounds 4-R are of the isolated products 4f؊i-Me with acid, efficient transformation to the correspondingly substituted bicyclo[3.2.1]octa-transformed to the correspondingly substituted bicyclo-[3.2.1]octanecarboxylates 5 by treatment with acid. 2Ј-Meth-necarboxylates 5 is observed. oxytricyclooctanes 4a؊d-Me are readily deprotonated to The bicyclo[3.2.1]octane ring system is a key structural by alkylation of the dienolates from 1a-Me and 1c-Bu with, respectively, methyl iodide and allyl bromide. component in a large variety of tri-and tetracyclic sesquiand diterpenes and their metabolites. [2] The basic skeleton Enone 2-Bzl was prepared by C-allylation of cyclohexane-1
Who reads Highly Functionalized Bicyclo[3.2.1]octane Derivatives from Readily Available 2′-Alkoxytricyclo[3.2.1.02,7]octanes: Building Blocks for Terpenes, Part I?
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- Author
- Armin de Meijere; Lazaros Hadjiarapoglou; Mathias Noltemeyer; Hans-Jürgen Gutke; Iris Klein; Dietrich Spitzner
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 1434-193X)
- Published
- 1998
- Language
- EN
- Field
- Chemistry (Physical Sciences)