Experimental study demonstrates the synthesis of the andrastin C cyclopenta[a]phenanthrene framework, highlighting stereoselective Diels-Alder and carbonyl ene reactions.
An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2-(methoxymethoxy)propanal 31.
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Okamoto et al. (2012) studied this question.
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