Stereoselective Synthesis of Functionalized Carbocycles and Heterocycles via an Ester Enolate Claisen/Ring-Closing Metathesis Manifold†,‡

1998 ◽  
Vol 63 (10) ◽  
pp. 3158-3159 ◽  
Author(s):  
John F. Miller ◽  
Andreas Termin ◽  
Kevin Koch ◽  
Anthony D. Piscopio
Keyword(s):  
Stereoselective Synthesis ◽  
Ring Closing Metathesis ◽  
Ester Enolate

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.

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Asymmetric Reduction ◽  
Cross Coupling ◽  
Membered Ring ◽  
Stille Reaction ◽  
Reaction Sequence ◽  
Ring Closing Metathesis ◽  
Synthetic Strategy ◽  
First Time

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Stereoselective Synthesis of the Naturally Occurring Lactones (−)-Osmundalactone and (−)-Muricatacine Using Ring-Closing Metathesis

2002 ◽  
Vol 2002 (15) ◽  
pp. 2649 ◽  
Author(s):  
Miguel Carda ◽  
Santiago Rodríguez ◽  
Florenci González ◽  
Encarnación Castillo ◽  
Alicia Villanueva ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Ring Closing Metathesis ◽  
Naturally Occurring
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