Synthesis and transannular Diels–Alder reaction of a 13-membered macrocyclic triene having a tetrasubstituted enol ether as dienophile | Zendy

Gervais Bérubé | Zendy; Pierre Deslongchamps | Zendy

Open Access

Synthesis and transannular Diels–Alder reaction of a 13-membered macrocyclic triene having a tetrasubstituted enol ether as dienophile

Author(s) -

Gervais Bérubé,

Pierre Deslongchamps

Publication year - 1990

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v90-062

Subject(s) - chemistry , diels–alder reaction , derivative (finance) , allyl alcohol , ether , cis–trans isomerism , alcohol , enol ether , enol , stereochemistry , medicinal chemistry , organic chemistry , catalysis , financial economics , economics

The syntheses of the acyclic triene trans–trans–cis27 and trans–trans–trans31 are described. Macrocyclization and concomitant transannular Diels–Alder reaction were performed with the chloride derivative obtained from the trans–trans–cis triene alcohol 27 yielding a mixture of the tricyclic compounds trans–syn–trans33 and cis–syn–cis34. On the other hand, macrocyclization of the chloride derived from trans–trans–trans triene 31 was not successful. Keywords: transannular process, Diels–Alder reaction, macrocyclic triene, macrocyclization, tricyclic compounds, organic synthesis.

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