Indole diterpene synthetic studies. 2. First-generation total synthesis of (-)-paspaline

RE Mewshaw, MD Taylor…

Index: Mewshaw, Richard E.; Taylor, Michael D.; Smith, Amos B. Journal of Organic Chemistry, 1989 , vol. 54, # 14 p. 3449 - 3462

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Citation Number: 44

Abstract

We record here a full account of the first total synthesis of (-)-paspaline (l), the simplest member of a rapidly growing class of architecturally complex diterpene indole alkaloids, many of which possess potent tremorgenic activity. In terms of sequential annulation, the strategy involves the following operations: DE-CDE-+ CDEF+ ABCDEF. Proceeding in 23 steps from Wieland-Miescher ketone, the synthesis afforded (-)-paspaline (1) in high ...