Synthetic Studies toward the Tetrapetalones: Diastereoselective Construction of a Putative Intermediate.

Org Lett

Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.

Published: February 2018

A strategy toward tetrapetalones was explored including a site-selective ethylenation of the silyl enol ether A to afford a quaternary stereocenter that serves in a stereogenic capacity. Regio- and diastereoselective reactions were observed in conjunction with the oxidative formation of cation B, which included subsequent selective formation of either carbon-oxygen or carbon-carbon bonds at the δ or ζ position on the seven-membered ring. The fourth ring was formed using a Stetter reaction.

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http://dx.doi.org/10.1021/acs.orglett.7b03500DOI Listing

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