The transformation of the bisabolyl cation in to a range of sesquiterpene natural products has been described in the literature (Hong, YJ; Tantillo, DJ. <i>J. Am. Chem. Soc.</i> 2014, <b>136</b>, 2450−2463). Hong and Tantillo proposed unifying mechanistic pathways by which the moncylcic bisabolyl cation is converted the into mono-, di- and tricyclic molecules containing an array of interesting structural features including 3-to-7-membered rings, fused rings, spiro centers, geometric and stereoisomers, and conjugated dienes. The sesquiterpene products of these pathways include barbatene, bazzanene, chamigrene, chamipinene, cumacrene, cuprenene, dunniene, isobazzanene, iso-g-bisabolene, isochamigrene, laurene, microbiotene, sesquithujene, sesquisabinene, thujopsene, trichodiene, and widdradiene. Now that the chemistry steps for the pathways leading to these products have been established we are focused on establishing a conformational library in database format of sesquterpene carbocation intermediates and products. We propose that analysis of this database will provide insight into the detailed stereoelectronic requirements of these chemically complex carbocation cascades.

Progress toward a conformational database for sesquiterpene reaction pathways

251st National Meeting (2016)

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