Tetrahedron Letters

Synthetic approaches toward the marine alkaloid prenostodione

JC Badenock, JA Jordan, GW Gribble

Index: Badenock, Jeanese C.; Jordan, Jason A.; Gribble, Gordon W. Tetrahedron Letters, 2013 , vol. 54, # 22 p. 2759 - 2762

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Citation Number: 5

Abstract

An efficient synthesis of the core of prenostodione (3) is described herein featuring the base condensation of BOC-protected indole diesters 21 and 24 with p-methoxybenzaldehyde (22) and 4-[(t-butyldimethylsilyl) oxy] benzaldehyde (26). Attempts at selective saponification of the resultant diesters yielded isoprenostodione (3a) bearing the ester functionality at the C-3 position of the indole ring.