Endiandric Acid D – Electrocyclic Reactions in Nature

6π Electrocyclic Reaction: disrotatory

Sn2

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The second step which has occurred by the 8pi system setting up a 6pi system. This part of the tandem reaction is disrotatory. Disrotatory ring closure can happen on either side of the system, over the top face or under the bottom face. To form endiandric acid D the disrotatory motion occurs over the top face, the orbitals move “inwardly”. This results in the two hydrogens pointing up.

Please note that here the substituents that end up on opposite sides are modelled by methyl groups. The berry coloured methyl is the allyl chain with a phenyl at the end, and the cyan coloured methyl is the carboxylic acid substituent.

 

Final Year Project 2013: Ilona Blee

Previous Step in Tandem

Other Option in Tandem – disrotatory to form Endiandric Acid E

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K. C. Nicolaou, N. A. Petasis, R. E. Zipkin and J. Uenishi, J. Am. Chem. Soc., 1982, 104, 5555–5557.

 

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