Investigations into an Anionic Oxy-Cope/Transannular Conjugate Addition Approach to 7,20-Diisocyanoadociane
Organic Letters2014Vol. 16(17), pp. 4368–4371
Citations Over TimeTop 10% of 2014 papers
Abstract
An anionic oxy-Cope/transannular conjugate addition approach to the potent antimalarial 7,20-diisocyanoadociane is presented. The unexpected formation of undesired diastereomers in the key reaction led to the structural reassignment of previous products of this type of cascade and a reevaluation of the reversibility of the transannular ring closure. During efforts to coax the reaction toward the desired product, a transannular ene reaction provided tricyclic compounds relevant to the kempane diterpenoids.
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