The first bioinspired and protecting group free total synthesis of the antibacterial sesquiterpenoid antroalbocin A has been achieved in five linear steps from a literature-known intermediate with an overall yield of 6.7%. An intramolecular Robinson annulation gave rapid access to the tricyclic enone as starting material for a photochemical domino process of deconjugation and sigmatropic 1,3-acyl shift. Herein we further describe studies towards the use of photolytic sigmatropic 1,3-acyl shifts in the synthesis of bridged terpenoid building blocks.Antroalbocin A (1), isolated in 2018 from the higher fungus Antrodiella albocinnamomea by Liu and co-workers, is a new antibacterial sesquiterpenoid. [1] Its unique structure shows a novel bridged 5/5/6 tricyclic system with three all carbon quaternary centers. Two of them are located in both bridgehead positions.

The first bioinspired and protecting group free total synthesis of the antibacterial sesquiterpenoid antroalbocin A has been achieved in five linear steps from a literature-known intermediate with an overall yield of 6.7%. An intramolecular Robinson annulation gave rapid access to the tricyclic enone as starting material for a photochemical domino process of deconjugation and sigmatropic 1,3-acyl shift. Herein we further describe studies towards the use of photolytic sigmatropic 1,3-acyl shifts in the synthesis of bridged terpenoid building blocks.Antroalbocin A (1), isolated in 2018 from the higher fungus Antrodiella albocinnamomea by Liu and co-workers, is a new antibacterial sesquiterpenoid. [1] Its unique structure shows a novel bridged 5/5/6 tricyclic system with three all carbon quaternary centers. Two of them are located in both bridgehead positions.

The first bioinspired and protecting group free total synthesis of the antibacterial sesquiterpenoid antroalbocin A has been achieved in five linear steps from a literature-known intermediate with an overall yield of 6.7%. An intramolecular Robinson annulation gave rapid access to the tricyclic enone as starting material for a photochemical domino process of deconjugation and sigmatropic 1,3 acyl shift. Herein we further describe studies towards the use of photolytic sigmatropic 1,3-acyl shifts in the synthesis of bridged terpenoid building blocks.