The Total Synthesis of Raistrickindole A

Thang Loi Pham; Patcharaporn Sae-Lao; Hannah Hui Min Toh; Dániel Csókás; Roderick W. Bates

doi:10.1021/acs.joc.2c02033

The Total Synthesis of Raistrickindole A

Thang Loi Pham, Patcharaporn Sae-Lao, Hannah Hui Min Toh, Dániel Csókás, Roderick W. Bates^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The total synthesis of raistrickindole A has been achieved, thereby confirming the proposed structure as an N-hydroxylated DKP. In the first but less selective approach, the DKP was built up by cyclization of a diastereoisomerically mixed N-hydroxylated dipeptide. In the second approach, the same DKP was constructed stereoselectively by the intramolecular Mitsunobu reaction of a hydroxamic acid. The synthesis was completed by a stereoselective oxidative cyclization.

Original language	English
Pages (from-to)	16111-16114
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	87
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.2c02033
Publication status	Published - Dec 2 2022
Externally published	Yes

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© 2022 American Chemical Society. All rights reserved.

ASJC Scopus Subject Areas

Organic Chemistry

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10.1021/acs.joc.2c02033

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AU - Sae-Lao, Patcharaporn

AU - Toh, Hannah Hui Min

AU - Csókás, Dániel

AU - Bates, Roderick W.

PY - 2022/12/2

Y1 - 2022/12/2

N2 - The total synthesis of raistrickindole A has been achieved, thereby confirming the proposed structure as an N-hydroxylated DKP. In the first but less selective approach, the DKP was built up by cyclization of a diastereoisomerically mixed N-hydroxylated dipeptide. In the second approach, the same DKP was constructed stereoselectively by the intramolecular Mitsunobu reaction of a hydroxamic acid. The synthesis was completed by a stereoselective oxidative cyclization.

AB - The total synthesis of raistrickindole A has been achieved, thereby confirming the proposed structure as an N-hydroxylated DKP. In the first but less selective approach, the DKP was built up by cyclization of a diastereoisomerically mixed N-hydroxylated dipeptide. In the second approach, the same DKP was constructed stereoselectively by the intramolecular Mitsunobu reaction of a hydroxamic acid. The synthesis was completed by a stereoselective oxidative cyclization.

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The Total Synthesis of Raistrickindole A

Abstract

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ASJC Scopus Subject Areas

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