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Updated: Feb 23, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Total Synthesis of (+)-Aplykurodinone-1
Bo Xu1, Wen Xun1, Tingzhong Wang2
1Guangzhou Institute of Biomedicine and Health, The University of the Chinese Academy of Sciences , 190 Kaiyuan Avenue, The Science Park of Guangzhou, Guangdong 510530, China.
Abstract:
Starting from (R)-citronellic acid and (R)-seudenol, the total synthesis of (+)-aplykurodinone-1, a highly degraded marine steroid, has been achieved in 11 steps and in 19% overall yield with excellent stereochemical control. In addition to the features such as an Ireland-Claisen rearrangement, an intramolecular carbonyl-ene cyclization, and an intramolecular Michael addition, the present synthetic strategy is accomplished without the use of protecting groups.

