Total Synthesis of Anticancer Agent EBC-23
Dodda Vasudeva Reddy1, Gowravaram Sabitha, Tadikamalla Prabhakar Rao
1Academy of Scientific and Innovative Research (AcSIR) , New Delhi 110020, India.
Organic Letters
|August 12, 2016
Summary
Researchers achieved the total synthesis of spiroketal EBC-23 using two distinct strategies from simple precursors. Key steps included gold-catalyzed cycloisomerization and acid-mediated spirocyclization, alongside a copper-catalyzed hydroboration.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Spiroketals are prevalent structural motifs in natural products.
- Efficient synthetic routes to complex spiroketals are highly sought after.
Purpose of the Study:
- To describe the total synthesis of spiroketal EBC-23.
- To explore divergent synthetic strategies for spiroketal formation.
Main Methods:
- Utilized gold-catalyzed cycloisomerization of alkynols.
- Employed acid-mediated spirocyclization of diketalketones.
- Applied a Cu(I)-P(Cy)3-catalyzed hydroboration of propargylic alcohols.
Main Results:
- Successfully achieved the total synthesis of spiroketal EBC-23.
- Demonstrated two divergent synthetic pathways.
- Established a highly regio- and stereocontrolled hydroboration protocol.
Conclusions:
- The developed synthetic routes offer efficient access to spiroketal EBC-23.
- The methodologies employed are valuable for constructing complex spiroketal structures.
