Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antfinflammatory agent mangicol A

• Published in: Tetrahedron Vol. 62; no. 22; pp. 5178 - 5194
• Main Authors: Pichlmair, Stefan, de Lera Ruiz, Manuel, Basu, Kallol, Paquette, Leo A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 29.05.2006
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; CONVENIENT SYNTHESIS; ORGANIC-SYNTHESIS; ASYMMETRIC-SYNTHESIS; ACID; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; intramolecular aldol cyclizations; EFFICIENT SYNTHESIS; PD-CATALYZED CYCLOISOMERIZATION; mangicols; enantioselective diene synthesis; chiral nonracemic substituted cyclopentadienones; ALLYLIC ALCOHOLS; Pd-catalyzed enyne cyclization; KINETIC RESOLUTION

A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladiu...