The synthesis of indole diterpenoids has long provided a fruitful area for scientific discovery. Tubingensin B is a complex alkaloid of this variety isolated from the fungus Aspergillus tubingensis. The natural product contains five stereocenters within a unique bicycle[3.2.2]nonane core, two of which are vicinal quaternary centers. This presentation will describe our approach to tubingensin B, which employs a heterocyclic aryne intermediate to construct the stereochemically complex framework of the natural product.

Synthetic efforts toward the total synthesis of tubingensin B

253rd National Meeting (2017)

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