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Reserpine

Natural product (-) reserpine from Indian snake root Indole alkaloid antipsychotic and antihypertension drug – rarely used today Original synthesis Woodward et al. 1958 Pentacyclic nucleus – stereoselective and regiospecific D/E ring system ( cis -hydroisoquinoline)

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Reserpine

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  1. Natural product (-) reserpine from Indian snake root Indole alkaloid antipsychotic and antihypertension drug – rarely used today Original synthesis Woodward et al. 1958 Pentacyclic nucleus – stereoselective and regiospecific D/E ring system (cis-hydroisoquinoline) Alternative epimer at stereogenic centre C-3 is undesired product isoreserpine Reserpine

  2. Syntheses reviewed: Total Synthesis of (±)-Reserpine Martin et al. (1985) Regiospecific and Stereoselective Syntheses of (±)-Reserpine and (-)-Reserpine Stork et al. (2005)

  3. Martin (1985) STRATEGY:

  4. Martin (1985)

  5. Martin (1985)

  6. Martin (1985)

  7. Martin (1985) Diels-Alder intramolecular cycloelimination

  8. Stork (2005) STRATEGY: Multiple strategies to subgoal Subgoal in 1st strategy:

  9. Stork (2005)

  10. Stork (2005) – 1st route to subgoal

  11. Stork (2005) – 1st route to subgoal

  12. Stork (2005) – 1st route to subgoal

  13. Stork (2005) – 2nd route to subgoal

  14. Stork (2005) – 2nd route to subgoal

  15. Stork (2005) Double Michael reaction

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