ScholarLens Back to search
2006•European Journal of Organic ChemistryRequires access

Total Synthesis of (+)‐Migrastatin

Sébastien Reymond, Janine Cossy

Open publisher page 27 citations

Abstract

Abstract (+)‐Migrastatin, an antimetastatic agent, was synthesized by using three ruthenium‐catalyzed metathesis reactions: a ring‐closing metathesis (RCM) to control the (Z)‐trisubstituted double bond at C11–C12, another RCM at C6–C7 to establish the macrolactone core, and a cross‐metathesis to install the glutarimide side chain at C16–C17. The stereogenic centers at C9, C10, C13, and C14 were introduced by using two stereoselective crotylmetalations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

About this research paper

What this paper is about

Abstract (+)‐Migrastatin, an antimetastatic agent, was synthesized by using three ruthenium‐catalyzed metathesis reactions: a ring‐closing metathesis (RCM) to control the (Z)‐trisubstituted double bond at C11–C12, another RCM at C6–C7 to establish the macrolactone core, and a cross‐metathesis to install the glutarimide side chain at C16–C17. The stereogenic centers at C9, C10, C13, and C14 were introduced by using two stereoselective crotylmetalations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Why it matters

OpenAlex reports 27 citations for this work. Citation counts describe recorded attention and do not establish research quality.

Key contribution

A contribution statement is not available in the OpenAlex record.

Method / approach

Method details are not available in the OpenAlex metadata.

Main findings

Findings are not separately available in the OpenAlex metadata.

Limitations

Limitations are not available in the OpenAlex metadata.

Applications

Application details are not available in the OpenAlex metadata.

Available abstract

Abstract (+)‐Migrastatin, an antimetastatic agent, was synthesized by using three ruthenium‐catalyzed metathesis reactions: a ring‐closing metathesis (RCM) to control the (Z)‐trisubstituted double bond at C11–C12, another RCM at C6–C7 to establish the macrolactone core, and a cross‐metathesis to install the glutarimide side chain at C16–C17. The stereogenic centers at C9, C10, C13, and C14 were introduced by using two stereoselective crotylmetalations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Key concepts: Stereocenter, Chemistry, Metathesis, Ring-closing metathesis, Total synthesis, Salt metathesis reaction, Stereochemistry, Stereoselectivity

Related papers

Related paper 1Related paper 2Related paper 3
Back to paper searchBrowse research topicsOriginal source
Total Synthesis of (+)‐Migrastatin — Research Paper | ScholarLens