Stereocontrolled Synthesis of (+)-Plagiogyrin A.
Plagiogyrin A (1) was first isolated from the fronds of Plagiogyria matsumureana. Structurally, it features an α-ketoaldehyde functional group in its hemiacetal form, fused in a cis-substituted lactone ring. We have successfully synthesized the skeleton of this natural product by employing a stereocontrolled aldol reaction followed by the installation of the α-ketoaldehyde moiety derived from the mild oxidation of an α-diazoketone. Finally, anhydrous acidic conditions released the protected diol and provided the required cyclized hemiacetal.
Department of Chemistry, College of Sciences, NC State University , Raleigh, North Carolina 27695, United States.
Yunlong
Y
Shi
Department of Chemistry, College of Sciences, NC State University , Raleigh, North Carolina 27695, United States.
Joshua G
JG
Pierce
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