Total synthesis of (.+-.)-coronafacic acid: use of anionic oxy-Cope rearrangements on aromatic substrates in synthesis

1980 ◽  
Vol 102 (7) ◽  
pp. 2463-2464 ◽  
Author(s):  
Michael E. Jung ◽  
James P. Hudspeth
Keyword(s):  
Total Synthesis ◽  
Coronafacic Acid ◽  
Aromatic Substrates ◽  
Cope Rearrangements

Total synthesis of d,l-coronafacic acid by an intermolecular Diels–Alder approach

1984 ◽  
Vol 62 (9) ◽  
pp. 1747-1750 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Montse Llinas-Brunet
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Keto Ester ◽  
Coronafacic Acid

An efficient total synthesis of d,l-coronafacic acid (2) has been achieved from 4-cyclopentene-1,3-dione (4). The synthesis involves keto ester 7 as a key intermediate that is conveniently prepared by the Diels–Alder addition of enedione 4 to ethyl 4-ethyl-2,4-pentadienoate (5).

Recent chemoenzymatic total syntheses of natural and unnatural products: Codeine, balanol, pancratistatin, and oseltamivir

2010 ◽  
Vol 82 (9) ◽  
pp. 1785-1796 ◽  
Author(s):  
Tomáš Hudlický
Keyword(s):  
Total Synthesis ◽  
Total Syntheses ◽  
Toluene Dioxygenase ◽  
Aromatic Substrates ◽  
Short Summary ◽  
Unnatural Products

Presented here is a short summary of the recent accomplishments in total synthesis in our laboratories. In particular, recent generations of the syntheses of pancratistatin derivatives, codeine, balanol, and oseltamivir (Tamiflu) are described in relation to their common chemoenzymatic origin in toluene-dioxygenase-mediated dioxygenation of aromatic substrates. Perspectives and projections are discussed in the conclusion.

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