Synthesis of mulinane diterpenoids

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Diterpenoids

Background:

• Mulinanes are biologically active tricyclic diterpenoids with diverse oxidation states.
• The synthesis of mulinanes presents challenges due to their complex structures.

Purpose of the Study:

• To achieve the first total synthesis of four mulinane natural products.
• To develop a divergent synthetic strategy for accessing the mulinane scaffold.

Main Methods:

• Utilized a diastereoselective anionic oxy-Cope rearrangement to establish the C8 stereocenter.
• Employed an unprecedented vinylogous Saegusa dehydrogenation reaction for C-ring functionalization.

Main Results:

• Successfully synthesized four distinct mulinane compounds.
• Demonstrated the utility of the developed synthetic methodology.

Conclusions:

• The reported synthetic route provides access to the challenging mulinane diterpenoid class.
• The novel reactions employed offer new tools for complex molecule synthesis.