A stereoselective synthesis of (+)-physoperuvine using a tandem aza-Claisen rearrangement and ring closing metathesis reaction

2009 ◽  
Vol 7 (13) ◽  
pp. 2678 ◽  
Author(s):  
Ahmed M. Zaed ◽  
Michael D. Swift ◽  
Andrew Sutherland
Keyword(s):  
Claisen Rearrangement ◽  
Stereoselective Synthesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis

scholarly journals A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring-closing metathesis

2009 ◽  
Vol 5 ◽  
Author(s):  
Palakodety Radha Krishna ◽  
Krishnarao Lopinti ◽  
K L N Reddy
Keyword(s):  
Stereoselective Synthesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Propargylic Alcohol ◽  
Key Steps

A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone was successfully completed. Key steps included the application of Carreira’s asymmetric alkynylation reaction to form a propargylic alcohol and subsequently lactone formation using the powerful ring-closing metathesis reaction.

scholarly journals Stereoselective Synthesis of the I–L Fragment of the Pacific Ciguatoxins

Toxins ◽  
2020 ◽  
Vol 12 (12) ◽  
pp. 740
Author(s):  
J. Stephen Clark ◽  
Michael Popadynec
Keyword(s):  
Stereoselective Synthesis ◽  
Ring System ◽  
Membered Ring ◽  
Hydroxyl Groups ◽  
Oxidation Reactions ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Selective Protection ◽  
Conjugate Reduction ◽  
The Pacific

The I–L ring system found in all the Pacific ciguatoxins has been prepared from a tricyclic precursor in a highly stereoselective manner. Subtle differences in the reactivity of the enones present in the seven- and eight-membered rings of the tricyclic ether starting material have been exploited to allow selective protection of the enone in the eight-membered ring. Subsequent distereoselective allylation of the seven-membered ring has been accomplished by a palladium-mediated Tsuji-Trost reaction. The K-ring methyl and hydroxyl groups have been installed in a highly stereoselective manner by sequential conjugate reduction and enolate oxidation reactions. Ring L has been constructed by a use of a novel relay ring-closing metathesis reaction to complete the tetracyclic framework, which possesses the functionality necessary for elaboration of rings I and L and the introduction of ring M.

A Double Ring Closing Metathesis Reaction in the Rapid, Enantioselective Synthesis of NK-1 Receptor Antagonists

2001 ◽  
Vol 3 (5) ◽  
pp. 671-674 ◽  
Author(s):  
Debra J. Wallace ◽  
Jonathan M. Goodman ◽  
Derek J. Kennedy ◽  
Antony J. Davies ◽  
Cameron J. Cowden ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Metathesis Reaction ◽  
Receptor Antagonists ◽  
Ring Closing Metathesis ◽  
Double Ring
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