1422044-23-2Relevant academic research and scientific papers
Unified Synthesis of 10-Oxygenated Lycopodium Alkaloids: Impact of C10-Stereochemistry on Reactivity
Saha, Mrinmoy,Li, Xin,Collett, Nathan D.,Carter, Rich G.
, p. 5963 - 5980 (2016/07/23)
The pronounced impact of the C10 stereochemistry on the successful construction of a polycyclic Lycopodium alkaloid scaffold has been explored. A wide range of reaction conditions and functionality were investigated to control a keto sulfone Michael addition to construct the C7-C12 linkage. An unexpected, overriding impact of the C10 stereochemistry in stereoselectivity and reaction rate in the Michael addition was observed. Furthermore, divergent reactivity of a conformationally accelerated, intramolecular Mannich cyclization based on the C10 stereochemistry was discovered. The successful execution of this synthetic route resulted in the total synthesis of all three known 10-oxygenated Lycopodium alkaloids: 10-hydroxylycopodine, paniculine, and deacetylpaniculine.
Toward a unified approach for the lycopodines: Synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine
Saha, Mrinmoy,Carter, Rich G.
, p. 736 - 739 (2013/04/10)
The enantioselective syntheses of 10-hydroxylycopodine, deacetylpaniculine, and paniculine have been accomplished through use of a common intermediate. Key steps in the synthetic sequence toward these lycopodium alkaloids include formation of the tricyclic core via a conformationally accelerated, intramolecular Mannich cyclization and an organocatalyzed, intramolecular Michael addition to form the C7-C12 linkage.
