95217-64-4Relevant academic research and scientific papers
Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline
Sharpe, Robert J.,Johnson, Jeffrey S.
, p. 9740 - 9766 (2015/10/12)
An enantioselective synthesis of the indole diterpenoid natural product paspaline is disclosed. Critical to this approach was the implementation of stereoselective desymmetrization reactions to assemble key stereocenters of the molecule. The design and execution of these tactics are described in detail, and a thorough analysis of observed outcomes is presented, ultimately providing the title compound in high stereopurity. This synthesis provides a novel template for preparing key stereocenters in this family of molecules, and the reactions developed en route to paspaline present a series of new synthetic disconnections in preparing steroidal natural products.
Indole Diterpene Synthetic Studies. 2. First-Generation Total Synthesis of (-)-Paspaline
Mewshaw, Richard E.,Taylor, Michael D.,Smith, Amos B.
, p. 3449 - 3462 (2007/10/02)
We record here a full account of the first total synthesis of (-)-paspaline (1), 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 enantiomeric purity.
