Search

Research has been conducted on the naphthalene building blocks. The alternate route developed for the synthesis of these building blocks is described.

The first total synthesis of ancistrocladidine 7,3'-linked naphthylisoquninoline alkaloid is completed, with the key feature of the synthesis being the formation of the extremely hindered biaryl linkage by ortho-arylation of a naphthol with an aryllead triacetate. Initial efforts were focused on the generation of a heteroaryl lead species, which would have allowed a convergent synthesis to be developed.

The isomerization-Claisen rearrangement (ICR) reactions of boron-substituted di(allyl) ethers, the properties of the derived beta-boryl aldehydes, and the utility of these species as conduits to Claisen adducts previously inaccessible from the ICR methodology are described. The merging of ICR methodology with ensuing Suzuki cross-coupling reactions will expand the utility of the ICR technology in various synthesis activities.

A study aimed at the broad exploitation of claisen-derived alpha-chiral aldehydes in synthesis activities, and developed highly stereoselective Claisen rearrangements from easily prepared di(allyl) ethers. The claisen rearrangements involved catalyzed olefin isomerization to generate the vinyl ether moiety followed by thermal sigmatropic rearrangement to afford syn-2,3-dialkyl-4-pentenal derivatives with high diastereoselectivity.