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ChemInform Abstract: Transannular Diels—Alder Reaction Studies with an Activated Dienophile. An Enantioselective Synthesis of an A.B.C.[6.6.6.] trans-syn-cis Tricycle.

✍ Scribed by L. BARRIAULT; S. G. OUELLET; P. DESLONGCHAMPS

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199807032

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✦ Synopsis

Transannular Diels-Alder Reaction Studies with an Activated Dienophile.

An Enantioselective Synthesis of an A.B.C.[6.6.6.] trans-syn-cis Tricycle.

-The synthesis of the chiral macrocycle (VI) starting from nerol (I), and its transannular Diels-Alder reaction (TADA) under thermal conditions affording tricycle (VII) is described. The TADA reaction is not observed under Lewis acid catalyzed conditions. The reasons for this behavior are discussed.

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