Total Synthesis of (+)-Raistrickindole A

Amy C. Jackson; Yong Sun Cho; Taehwan Hwang; John C. Park; John Wood

doi:10.1021/acs.orglett.6c00417

March 3, 2026Organic LettersOpen Access

Total Synthesis of (+)-Raistrickindole A

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Key Points

The aim is to complete the total synthesis of the alkaloid (+)-raistrickindole A.
Used a stereochemical relay strategy for synthesis.
Employed an intermolecular nitroso Diels-Alder cycloaddition.
Achieved regio- and diastereoselective core formation of a 3,4-dihydro-1,2-oxazine.
Implemented a stereoselective Mukaiyama hydration in the later stages.
Successfully completed the total synthesis of (+)-raistrickindole A.
Demonstrated effective regio- and diastereoselectivity in cycloaddition.
Showed that the hydration step could be performed stereoselectively.

Implication

Research demonstrates the total synthesis of indole alkaloid (+)-raistrickindole A, highlighting its complex formation.

Abstract

A total synthesis of the indole diketopiperazine alkaloid (+)-raistrickindole A has been completed. The synthesis employs a stereochemical relay strategy wherein an intermolecular nitroso Diels-Alder cycloaddition regio- and diastereoselectively delivers a 3,4-dihydro-1,2-oxazine core, which, in turn, enables a subsequent stereoselective Mukaiyama hydration.

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Cite This Study

Jackson et al. (2026) studied this question.

synapsesocial.com/papers/69aa6f0d531e4c4a9ff5935e https://doi.org/10.1021/acs.orglett.6c00417

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Total Synthesis of (+)-Raistrickindole A

Key Points

Implication

Abstract

Discussion

Cite This Study

Total Synthesis of (+)-Raistrickindole A

Key Points

Implication

Abstract

Discussion

Cite This Study

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