Fukuyama indole synthesis

[2] Most commonly tributyltin hydride is utilized as the reducing agent, with azobisisobutyronitrile (AIBN) as a radical initiator.

In addition the reaction is not stereospecific, in that both the cis and trans isoform can be used to obtain the desired product.

This reaction is a one-pot synthesis and results in yields ranging from 50% to 98% depending on the substituent.

The Fukuyama Indole synthesis can generate a range of different substituents at the 2,3 position that were previously unattainable without a protecting group on the nitrogen in the ring.

In addition, the fukuyama reaction plays a role in the syntheses of indolocarbazoles,[5] biindolyls,[5] and the total synthesis of vincadifformine and tabersonine.

Fukuyama Indole Synthesis with either starting material.
Fukuyama Indole Synthesis with either starting material.
Step-wise mechanism of Fukuyama Indole Synthesis starting with the Isocyano substituent.
Step-wise mechanism of Fukuyama Indole Synthesis starting with the Isocyano substituent.
Step-wise mechanism of the Fukuyama Indole Synthesis starting with the alkenylthioanilide substituent.
Step-wise mechanism of the Fukuyama Indole Synthesis starting with the alkenylthioanilide substituent.
Example Reaction for Fukuyama Synthesis.
Example Reaction for Fukuyama Synthesis.
Possible next step synthesis reactions working with the 2-iodoindoles from the Fukuyama Synthesis.
Possible next step synthesis reactions working with the 2-iodoindoles from the Fukuyama Synthesis.
Sample Fukuyama Indole Reaction Step in the Synthesis of Vinblastine
Sample Fukuyama Indole Reaction Step in the Synthesis of Vinblastine