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Abstract
The cyrneine diterpenoids represent a structurally intriguing subfamily of cyathane diterpenoids and could significantly induce neurite outgrowth. Therefore, the efficient synthesis of these natural products is of great importance. Herein, we present a route for the collective synthesis of cyrneines A, B, and glaucopine C. As the key precursor, the 5-6-6-tricyclic scaffold is efficiently constructed by employing a mild Suzuki coupling of heavily substituted nonactivated cyclopentenyl triflate and a chelation-controlled regiospecific Friedel-Crafts cyclization as key transformations. The stereoselective installation of the all-carbon quaternary center at C6 ring junction of the tricycle is achieved via Birch reductive methylation. Subsequently, a carbenoid-mediated ring expansion furnishes the essential 5-6-7-tricyclic core. Finally, manipulation of this core by several appropriately orchestrated conversions accomplishes a more step-economic synthesis of cyrneine A (20 steps), and the first synthesis of cyrneine B (24 steps) and glaucopine C (23 steps).
Highlights
The cyrneine diterpenoids represent a structurally intriguing subfamily of cyathane diterpenoids and could significantly induce neurite outgrowth
The cyathane diterpenoids compose a large family of natural products with greater than 100 members[1,2,3]
Biological evaluation revealed that cyathane diterpenoids exhibit a rich variety of biological activities such as antibiotics, antimicrobial, antitumor, antiinflammatory, and most significantly, nerve growth factor (NGF)regulating properties
Summary
The cyrneine diterpenoids represent a structurally intriguing subfamily of cyathane diterpenoids and could significantly induce neurite outgrowth. A carbenoid-mediated ring expansion furnishes the essential 5-6-7-tricyclic core. Manipulation of this core by several appropriately orchestrated conversions accomplishes a more step-economic synthesis of cyrneine A (20 steps), and the first synthesis of cyrneine B (24 steps) and glaucopine C (23 steps). The cyathane diterpenoids compose a large family of natural products with greater than 100 members[1,2,3]. These molecules feature a common 5-6-7 fused tricarbocyclic core with most of which possessing two all-carbon quaternary stereocenters at the ring junctions with anti-orientation. Of note are important contributions from the groups of Nakada[2], Ward[4,5], Trost[6,7], Danishefsky[8], Stoltz[9], Phillip[10], Reddy[11], Snider[12,13], and others[14,15]
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