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The first total synthesis of natural grenadamide. | LitMetric

The first total synthesis of natural grenadamide.

Org Biomol Chem

Department of Chemistry, University of Adelaide, South Australia 5005, Australia.

Published: January 2006

AI Article Synopsis

  • A new method is introduced to efficiently synthesize the naturally occurring form of grenadamide using a specific starting material called a 3,6-disubstituted 1,2-dioxine.
  • This synthesis technique enables the creation of various grenadamide derivatives by changing the cyclopropyl carbons at positions 2 and 3, allowing access to both enantiomers.
  • The study also provides insights into how phosphorus aids in the process of deprotonation for 1,2-dioxines.

Article Abstract

A concise, high yielding route to the naturally occurring enantiomer of grenadamide utilizing a 3,6-disubstituted 1,2-dioxine starting material is presented. The route allows for ease in synthesizing grenadamide derivatives varying at cyclopropyl carbons 2 and 3, with access to both enantiomers. Evidence for phosphorus-assisted deprotonation of 1,2-dioxines is also discussed.

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Source
http://dx.doi.org/10.1039/b513774hDOI Listing

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