Synthesis of angiolam A

Area of Science:

• Organic Chemistry
• Total Synthesis
• Natural Products Chemistry

Background:

• Angiolam A is a complex natural product with a unique structure.
• Previous synthetic efforts have not achieved a total synthesis of angiolam A.

Purpose of the Study:

• To achieve the first total synthesis of angiolam A.
• To determine the absolute configuration of angiolam A.

Main Methods:

• The synthesis employed vinylogous Mukaiyama aldol reactions and conjugate reduction.
• Macrolactamization was achieved using the Witzeman protocol.
• Optical rotation was compared to isolation data.

Main Results:

• The total synthesis of angiolam A was successfully completed in 18 steps.
• The absolute configuration of angiolam A was determined to be opposite to the initially proposed structure.

Conclusions:

• The first total synthesis of angiolam A provides a reliable route to the compound.
• The study corrects the proposed absolute configuration of angiolam A based on synthetic evidence.