Studies directed toward the total synthesis of retigeranic acid

Smith, Ralph Stephen (1984) Studies directed toward the total synthesis of retigeranic acid. Masters thesis, Memorial University of Newfoundland.

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Abstract

Studies directed at the total synthesis of retigeranic acid (1) have revealed that compounds of type 81a and 87 cyclize in intramolecular fashion to give the conjoint ring systems 91 and 90 rather than the fused bicyclo [3.3.0] octanes 48 and 88. Increasing the acidity of the γ-proton did not result in alkylative cyclization. -- The Wittig reagents 124, 125, and 126 have been synthesized and shown to react in normal fashion with aldehydes to give enol-ether-dienes such as 128 and α,β-unsaturated ketones 129 after hydrolysis. A route to a suitable triene 111 for the construction of the hydrindane portion of retigeranic acid has been developed, but unfortunately conditions were not found that allowed the intramolecular Diels-Alder reaction to proceed.

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