Indole diterpenoids comprise a vast and architecturally intriguing class of alkaloids, which has long provided a fruitful area for scientific discovery. Tubingensin A is a complex alkaloid of this variety isolated from the fungus <i>Aspergillus tubingensis</i>. Structurally, it contains four contiguous stereocenters, two of which are vicinal quaternary centers. Our laboratory has accomplished a 9-step (longest linear sequence) synthesis of tubingensin A using a reactive heterocyclic aryne intermediate to construct the challenging vicinal quaternary centers. Additionally, we are pursuing the application of this strategy to build tubingensin B, which contains an additional stereocenter and a unique bicyclo[3.2.2]nonane core. Progress toward its total synthesis will be presented.

Unified synthetic strategy toward the tubingensin alkaloids

251st National Meeting (2016)

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