Stereoselective Total Syntheses of Polyacetylene Plant Metabolites via Ester-Tethered Ring Closing Metathesis

2017 ◽  
Vol 82 (3) ◽  
pp. 1743-1760 ◽  
Author(s):  
Bernd Schmidt ◽  
Stephan Audörsch
Keyword(s):  
Plant Metabolites ◽  
Ring Closing Metathesis ◽  
Total Syntheses

Enantioselective formal total syntheses of Clavukerin A and isoclavukerin A via a ring-closing metathesis reaction

2010 ◽  
Vol 21 (6) ◽  
pp. 746-750 ◽  
Author(s):  
Adusumilli Srikrishna ◽  
Vijendra H. Pardeshi ◽  
Gedu Satyanarayana
Keyword(s):  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Total Syntheses

Stereoselective Total Syntheses of (3R,5R)-Sonnerlactone and (3R,5S)-Sonnerlactone

2017 ◽  
Vol 12 (9) ◽  
pp. 1934578X1701200
Author(s):  
Supriya Ghanty ◽  
P. Rasvan Khan ◽  
B. V. Subba Reddy
Keyword(s):  
Malic Acid ◽  
Ring Closing Metathesis ◽  
Total Syntheses ◽  
Key Steps ◽  
Barbier Allylation

A highly convergent and concise total syntheses of (3 R,5 R)-Sonnerlactone and (3 R,5 S) Sonnerlactone from a readily available L-malic acid is described. The following series of reactions such as Barbier allylation, photochemical esterification and Ring Closing Metathesis (RCM) are utilized as key steps to accomplish their syntheses.

Total Syntheses of New Proansamitocin Derivatives by Ring-Closing Metathesis

Synlett ◽  
2007 ◽  
Vol 2007 (08) ◽  
pp. 1264-1268 ◽  
Author(s):  
Andreas Kirschning ◽  
Axel Meyer
Keyword(s):  
Ring Closing Metathesis ◽  
Total Syntheses

scholarly journals Recent Advances in Total Synthesis via Metathesis Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (19) ◽  
pp. 3749-3786 ◽  
Author(s):  
Francisco Sarabia ◽  
Iván Cheng-Sánchez
Keyword(s):  
Total Synthesis ◽  
Tandem Reactions ◽  
Alkyne Metathesis ◽  
Enyne Metathesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Total Syntheses ◽  
Cross Metathesis ◽  
Carbon Carbon Bonds ◽  
Metathesis Reactions

The metathesis reactions, in their various versions, have become a powerful and extremely valuable tool for the formation of carbon–carbon bonds in organic synthesis. The plethora of available catalysts to perform these reactions, combined with the various transformations that can be accomplished, have positioned the metathesis processes as one of the most important reactions of this century. In this review, we highlight the most relevant synthetic contributions published between 2012 and early 2018 in the field of total synthesis, reflecting the state of the art of this chemistry and demonstrating the significant synthetic potential of these methodologies.1 Introduction2 Alkene Metathesis in Total Synthesis2.1 Total Synthesis Based on a Ring-Closing-Metathesis Reaction2.2 Total Synthesis Based on a Cross-Metathesis Reaction2.3 Strategies for Selective and Efficient Metathesis Reactions of Alkenes2.3.1 Temporary Tethered Ring-Closing Metathesis2.3.2 Relay Ring-Closing Metathesis2.3.3 Stereoselective Alkene Metathesis2.3.4 Alkene Metathesis in Tandem Reactions3 Enyne Metathesis in Total Synthesis3.1 Total Syntheses Based on a Ring-Closing Enyne-Metathesis Reaction3.2 Total Syntheses Based on an Enyne Cross-Metathesis Reaction3.3 Enyne Metathesis in Tandem Reactions4 Alkyne Metathesis in Total Synthesis4.1 Total Synthesis Based on a Ring-Closing Alkyne-Metathesis Reaction4.2 Other Types of Alkyne-Metathesis Reactions5 Conclusions

The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol

2001 ◽  
Vol 79 (11) ◽  
pp. 1668-1680 ◽  
Author(s):  
Darren J Dixon ◽  
Alison C Foster ◽  
Steven V Ley
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Selective Hydrogenation ◽  
Protecting Group ◽  
Ring Closing Metathesis ◽  
Total Syntheses ◽  
Key Steps

The total syntheses of the polyhydroxylated macrolactone (+)-aspicilin and a diastereoisomer have been achieved via a concise route, starting from the spatially desymmetrized (R',R',R,S)-2,3-butanediacetal-protected butane tetrol 13. The key steps include a regioselective silyl protection of 13 and a stereoselective Lewis acid mediated addition of allyltributylstannane to the equatorially disposed aldehyde of 4. Macrocyclization is achieved using ring closing metathesis, after which selective hydrogenation and protecting group removal yields the natural product.Key words: aspicilin, butanediacetal, desymmetrization, macrolactone, metathesis.

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