Synthesis of a bicyclo[5.3.1]undecene by a facile domino enyne cross-metathesis/IMDA

Kaliappan, Krishna P.; Ravikumar, Velayutham; Pujari, Sandip A.

doi:10.1016/j.tetlet.2005.11.144

Cited by 34 publications

(10 citation statements)

References 63 publications

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“…A similar EYCM/intramolecular DA strategy was used in 2006 for the synthesis of bicyclo[3.5.1]undecene, the structural unit present in many natural products including Taxol [60].…”

Section: Enyne Cross Metathesismentioning

confidence: 99%

Application of Cross Metathesis in Diene and Polyene Synthesis

Wojtkielewicz

2013

COS

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Olefin metathesis has become a useful method in organic synthesis, rivaling palladium catalyzed C-C bond forming reactions as well as more traditional olefination processes. Olefin cross metathesis (CM) emerged later than ring closing metathesis and ring opening metathesis polymerization due to poor selectivity control. However, after the discovery of more active second generation catalysts and elaboration by Grubbs of an empirical model to predict the outcome of these reactions, cross metathesis has found wide application in the synthesis of various alkenes including those that are sterically demanding or highly functionalized. In recent years enyne cross metathesis and metathetic coupling between alkene and diene or polyene were widely tested as alternative, convenient methods of diene and polyene preparation. In this review the application of ene-diene CM, ene-polyene CM, diene-polyene CM, ene-yne CM and alkene CM combined with other reactions in the synthesis of conjugated dienes and polyenes is presented. The aim of this article is to demonstrate not only the scope of CM application in the synthesis of conjugated dienes and polyenes but also its limitations associated mainly with problems of regio-and stereoselectivity control and how the encountered difficulties led to a better understanding of these processes and the discovery of more effective reaction conditions.

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“…A similar EYCM/intramolecular DA strategy was used in 2006 for the synthesis of bicyclo[3.5.1]undecene, the structural unit present in many natural products including Taxol [60].…”

Section: Enyne Cross Metathesismentioning

confidence: 99%

Application of Cross Metathesis in Diene and Polyene Synthesis

Wojtkielewicz

2013

COS

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“…[31] The enyne 87, synthesized from lactol 86 (Scheme 14) was subjected to a domino cross-enyne metathesis with ethylene and IMDA with Grubbs' catalyst 2 in toluene to afford bicyclo[5.3.1]undecene 88. [31] After synthesizing the AB-ring skeleton of taxol, the same group extended this domino strategy for the synthesis of taxaoxa-sugar hybrid. The aim was to develop simpler analogues of taxol by synthesizing hybrid structures of taxol and screen them for biological activity.…”

Section: Domino Rom/rcm Reactionmentioning

confidence: 99%

Recent Developments on Domino Metathesis Reactions in India

Nandurdikar

Kaliappan²

2012

Chimia

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“…Kaliappan et al described an efficient domino enyne cross‐metathesis/intramolecular Diels–Alder (IMDA) reaction for the construction of bicyclo[5.3.1]undecenes 82. The strategy, first implemented in the synthesis of tricyclic derivative 147 , is outlined in Scheme .…”

Section: Enyne Cross‐metathesis (Eycm)mentioning

confidence: 99%

Metathesis Reactions of Carbohydrates: Recent Highlights in Alkyne Metathesis

López

Plumet

2011

Eur J Org Chem

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Metathesis processes play a prominent role in the development of useful synthetic transformations because of their mildness and tolerance of functional groups. On the other hand, carbohydrates have gained well‐deserved importance in the study of biological processes. This review summarizes a decade of research in the application of alkyne metathesis (AM) reactions in some of its variants to carbohydrates and carbohydrate‐related compounds.

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Synthesis of a bicyclo[5.3.1]undecene by a facile domino enyne cross-metathesis/IMDA

Cited by 34 publications

References 63 publications

Application of Cross Metathesis in Diene and Polyene Synthesis

Application of Cross Metathesis in Diene and Polyene Synthesis

Recent Developments on Domino Metathesis Reactions in India

Metathesis Reactions of Carbohydrates: Recent Highlights in Alkyne Metathesis

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