Tetrahedron letters

Synthetic studies of zoanthamine alkaloids. Stereoselective synthesis of the ABC ring system of norzoanthamine by an intramolecular Diels–Alder reaction

M Sakai, M Sasaki, K Tanino, M Miyashita

Index: Sakai, Mio; Sasaki, Minoru; Tanino, Keiji; Miyashita, Masaaki Tetrahedron Letters, 2002 , vol. 43, # 9 p. 1705 - 1708

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Citation Number: 31

Abstract

Stereoselective synthesis of the ABC ring system of norzoanthamine having five asymmetric centers including two quaternary carbon atoms has been successfully accomplished by an intramolecular Diels–Alder reaction. A key intermediate for the Diels–Alder reaction was efficiently and stereoselectively synthesized by a tandem conjugate addition–aldol strategy and subsequent photosensitized oxidation of a furan derivative.