Tandem Asymmetric Ring-Opening/Cross Metathesis (AROM/CM) or Tandem Asymmetric Ring-Opening/Ring-Closing Metathesis (AROM/RCM)

2011 ◽  
pp. 1
Author(s):  
S. K. Collins
Keyword(s):  
Ring Opening ◽  
Ring Closing Metathesis ◽  
Cross Metathesis ◽  
Asymmetric Ring Opening

Tandem Catalytic Asymmetric Ring-Opening Metathesis/Ring-Closing Metathesis

2000 ◽  
Vol 122 (8) ◽  
pp. 1828-1829 ◽  
Author(s):  
Gabriel S. Weatherhead ◽  
J. Gair Ford ◽  
Erik J. Alexanian ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Ring Opening ◽  
Ring Closing Metathesis ◽  
Catalytic Asymmetric ◽  
Asymmetric Ring Opening

scholarly journals Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C 2-symmetric building block: a strategy for the synthesis of decanolide natural products

2013 ◽  
Vol 9 ◽  
pp. 2544-2555 ◽  
Author(s):  
Bernd Schmidt ◽  
Oliver Kunz
Keyword(s):  
Building Block ◽  
Ring Opening ◽  
Kinetic Resolution ◽  
Membered Ring ◽  
Ring Closure ◽  
Ring Closing Metathesis ◽  
Cross Metathesis ◽  
Key Steps ◽  
A Site ◽  
Site Selective

Starting from the conveniently available ex-chiral pool building block (R,R)-hexa-1,5-diene-3,4-diol, the ten-membered ring lactones stagonolide E and curvulide A were synthesized using a bidirectional olefin-metathesis functionalization of the terminal double bonds. Key steps are (i) a site-selective cross metathesis, (ii) a highly diastereoselective extended tethered RCM to furnish a (Z,E)-configured dienyl carboxylic acid and (iii) a Ru–lipase-catalyzed dynamic kinetic resolution to establish the desired configuration at C9. Ring closure was accomplished by macrolactonization. Curvulide A was synthesized from stagonolide E through Sharpless epoxidation.

Sign in / Sign up

Export Citation Format

Share Document