An Application to Natural Products Synthesis Sterpurene

A relatively recent application to natural product synthesis stems from efforts to synthesize a sesquiterpene called 1-sterpurene 7 [17]. This substance is thought to be the causative agent of the so-called silver leaf disease that affects certain species of shrubs and trees. The strategy focuses on three key steps (a) electrochemical cyclization of the bis unsaturated ester 11 to produce the five-membered ring of 10, (b) a Ruhlman-modified acyloin condensation to 

Electrode Proton source Trans/cis ratio Yield (%) Additive  

This example aside, the utility of the electrohydrocyclization reaction in the assembly of natural products remains essentially untapped. The reason for this observation is not entirely clear. Consider, for example, the rapid and efficient construction of the perhydrophenanthrene skeleton as exemplified by the conversion illustrated below [18]. The reaction is stereospecific, leading to the trans-anti-trans ring fused adduct 13 in a 65 to 72% yield. It takes little thought to imagine the application of this powerful transformation to the synthesis of steroids. Yet, this opportunity has not b n realized. 

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