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Route Optimization and Synthesis of Taxadienone

By Krasutsky, Sergiy G.; Jacobo, Sheila H.; Tweedie, Scott R.; Krishnamoorthy, Ravi; Filatov, Alexander S.

View Resource (DOI)

Category

Peer-reviewed journal

Published on CMKC

Abstract

Early process development toward the scalable production of taxadienone on a decagram scale is described. A continuous flow reactor was employed to safely run a potentially hazardous cyclopropane ring opening. The route featured two copper-mediated additions, a Diels–Alder reaction and a palladium-catalyzed Negishi coupling, to construct the final structure.

Journal

Organic Process Research & Development. Volume 19, 2015, 284–289

DOI

10.1021/op500314c

Type of publication

Peer-reviewed journal

Affiliations

  • AMRI
  • University at Albany

Article Classification

Research Article

Classification Areas

  • Intermediate

Tags

  1. copper-mediated additions
  2. Diels–Alder reaction
  3. Intermediate
  4. Negishi coupling
  5. Research Article
  6. Taxadienone