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.

Progress Towards the Stereoselective Synthesis of 3,6-Disubstituted 1,2-Diamino-4-cyclohexenes by Ring Closing Metathesis Reaction.

ChemInform ◽  
2003 ◽  
Vol 34 (15) ◽  
Author(s):  
Stefano Grilli ◽  
Gianluca Martelli ◽  
Diego Savoia ◽  
Carla Zazzetta
Keyword(s):  
Stereoselective Synthesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis

Studies towards the Synthesis of the Pyrido[1,2-a]azepine Alkaloids

2021 ◽  
Vol 18 ◽  
Author(s):  
DauXuan Duc
Keyword(s):  
Ring Structure ◽  
Bicyclic Compound ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Key Steps

A study towards the synthesis of the pyrido[1,2-a]azepine alkaloids is described. The bicyclic compound 1 containing the A-B core ring structure was synthesized in 17 steps in 1.7 % overall yield starting from 4-pentyn-1-ol. The key steps involve an oxidation of 1,4 diol to lactone and an ene-yne ring closing metathesis reaction.

Chiron approach for the total synthesis of brevipolide M

Synlett ◽  
2022 ◽  
Author(s):  
Yang Liu ◽  
Ziyang Zhao ◽  
Chao Hu ◽  
Chuanfang Zhao ◽  
Jun Liu ◽  
...  
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring Closing Metathesis ◽  
One Pot ◽  
Double Bond Migration ◽  
Key Steps

An efficient stereoselective synthesis of brevipolide M was established in 13 linear steps and 17.8% overall yields base on chiron approach. The key steps of our synthesis involved tandem homologation / tetrahydrofuran cyclization and sequential ring-closing metathesis (RCM) / double-bond migration in one-pot processes.

Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction

2011 ◽  
Vol 22 (11) ◽  
pp. 1161-1168 ◽  
Author(s):  
Merve Çayir ◽  
Sema Demirci ◽  
Serdar Sezer ◽  
Cihangir Tanyeli
Keyword(s):  
Stereoselective Synthesis ◽  
Optically Active ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis

A Stereoselective Synthesis of the ACE Inhibitor Trandolapril

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 813-816 ◽  
Author(s):  
Slim Chiha ◽  
Matthias Spilles ◽  
Jörg-Martin Neudörfl ◽  
Hans-Günther Schmalz
Keyword(s):  
Acid Derivative ◽  
Building Block ◽  
Ace Inhibitor ◽  
Stereoselective Synthesis ◽  
Pyroglutamic Acid ◽  
Ring Closing Metathesis ◽  
12 Steps ◽  
Key Steps

A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the α-allylation of a protected l-pyroglutamic acid derivative, a highly diastereoselective Hosomi–Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

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.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

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