Total synthesis of (-)-acetylaranotin

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Natural Product Synthesis

Background:

• (-)-Acetylaranotin is a natural product with a complex structure.
• Efficient synthetic routes are crucial for accessing complex molecules like (-)-acetylaranotin.
• The dihydrooxepine ring is a key structural feature of (-)-acetylaranotin.

Purpose of the Study:

• To develop an efficient total synthesis of (-)-acetylaranotin.
• To establish novel methodologies for constructing the dihydrooxepine core.
• To utilize readily available starting materials for the synthesis.

Main Methods:

• The synthesis employs a vinylogous Rubottom oxidation for C-C bond formation.
• A regioselective Baeyer-Villiger oxidation is utilized for epoxide formation.
• The route starts from commercially available L-Cbz-tyrosine (benzyloxycarbonyl-protected tyrosine).

Main Results:

• The characteristic dihydrooxepine ring was efficiently constructed from cyclohexenone.
• (-)-Acetylaranotin was synthesized in a total of 22 steps.
• The synthetic strategy proved effective for accessing the target molecule.

Conclusions:

• The developed synthetic route provides an efficient pathway to (-)-acetylaranotin.
• The key oxidation reactions are crucial for the construction of the dihydrooxepine moiety.
• This synthesis showcases a viable strategy for complex natural product preparation.