Skip to main content

Introduction of a New Stereocenter on C1-Functionalized 8-Oxabicyclo[3.2.1] oct-6-en 3-ones by a Regio- and Stereoselective Electrophilic Addition. Obtention of Polyfunctionalized Cycloheptanes with Five Stereocenters

Buy Article:

$55.00 plus tax (Refund Policy)

A methodology to obtain polyfunctionalized cycloheptane synthons, with five stereocenters, is presented. The precursors are C1-functionalized 8-oxabicyclo[3.2.1]oct-6-en-3-ones, obtained by a [4+3] cycloaddition reaction. The stereoselective reduction of the carbonyl group on C3 of these cycloadducts, followed by an electrophilic addition of organic acids on the C6-C7 double bond, under controlled conditions, allows the introduction of a new stereocenters on C6. The introduction of this new substituent on C6 takes place in a regio- and stereoselective way by a preferential exo attack on the oxabicyclic substrates. This synthetic methodology is versatile enough to allow the preparation of a wide variety of polypropionate building blocks, with applications to the synthesis of natural products with biological interest.
No References
No Citations
No Supplementary Data
No Data/Media
No Metrics

Keywords: cycloaddition reaction; cycloheptane synthons; electrophilic addition; oxabicyclo oct-en-one

Document Type: Review Article

Affiliations: Departamento de Quimica Organica, Universidad de Barcelona, c/ Martí i Franques 1-11, 08028-Barcelona, Spain.

Publication date: 2005-08-01

More about this publication?
  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
  • Access Key
  • Free content
  • Partial Free content
  • New content
  • Open access content
  • Partial Open access content
  • Subscribed content
  • Partial Subscribed content
  • Free trial content
Cookie Policy
Cookie Policy
Ingenta Connect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more