ChemInform Abstract: Synthesis of Cycloheptanoid Natural Products via a Tandem 5-exo-Cyclization/Claisen Rearrangement Process

ChemInform ◽  
2011 ◽  
Vol 42 (10) ◽  
pp. no-no ◽  
Author(s):  
Timo V. Ovaska
Keyword(s):  
Natural Products ◽  
Claisen Rearrangement ◽  
Rearrangement Process

The Claisen rearrangement in the syntheses of bioactive natural products

Tetrahedron ◽  
2013 ◽  
Vol 69 (34) ◽  
pp. 6921-6957 ◽  
Author(s):  
K.C. Majumdar ◽  
Raj Kumar Nandi
Keyword(s):  
Natural Products ◽  
Claisen Rearrangement ◽  
Bioactive Natural Products

A Domino Copper-Catalyzed C−O Coupling−Claisen Rearrangement Process

2003 ◽  
Vol 125 (17) ◽  
pp. 4978-4979 ◽  
Author(s):  
Gero Nordmann ◽  
Stephen L. Buchwald
Keyword(s):  
Claisen Rearrangement ◽  
Rearrangement Process

Asymmetric Synthesis of a Hydroxylated Nine-membered Lactone from Tartaric Acid using the Claisen Rearrangement

2010 ◽  
Vol 63 (3) ◽  
pp. 529 ◽  
Author(s):  
Leon S.-M. Wong ◽  
Kathleen A. Turner ◽  
Jonathan M. White ◽  
Andrew B. Holmes ◽  
John H. Ryan
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Tartaric Acid ◽  
Claisen Rearrangement ◽  
Cyclic Carbonate ◽  
Thermal Elimination ◽  
Ketene Acetal ◽  
Medium Ring

The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products.

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