Convergent total syntheses of the amaryllidaceae alkaloids lycoranine A, lycoranine B, and 2-methoxypratosine

Hye Sun Kim; Martin G. Banwell; Anthony C. Willis

doi:10.1021/jo4006987

Convergent total syntheses of the amaryllidaceae alkaloids lycoranine A, lycoranine B, and 2-methoxypratosine

Hye Sun Kim, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

20 Citations (Scopus)

Abstract

The title alkaloids, 1, 2, and 3 respectively, have been prepared in a convergent manner by two related routes. The superior one involves C-H functionalization of the relevant 5-methoxyindole at C-7 using Hartwig's protocol and thus forming the corresponding borolated indole that could be coupled with the requisite 2-bromobenzoate to deliver the title natural products. Single crystal X-ray analyses of the synthetically derived samples of compounds 1 and 2 are reported.

Original language	English
Pages (from-to)	5103-5109
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	78
Issue number	10
DOIs	https://doi.org/10.1021/jo4006987
Publication status	Published - 17 May 2013

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abstract = "The title alkaloids, 1, 2, and 3 respectively, have been prepared in a convergent manner by two related routes. The superior one involves C-H functionalization of the relevant 5-methoxyindole at C-7 using Hartwig's protocol and thus forming the corresponding borolated indole that could be coupled with the requisite 2-bromobenzoate to deliver the title natural products. Single crystal X-ray analyses of the synthetically derived samples of compounds 1 and 2 are reported.",

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AU - Willis, Anthony C.

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AB - The title alkaloids, 1, 2, and 3 respectively, have been prepared in a convergent manner by two related routes. The superior one involves C-H functionalization of the relevant 5-methoxyindole at C-7 using Hartwig's protocol and thus forming the corresponding borolated indole that could be coupled with the requisite 2-bromobenzoate to deliver the title natural products. Single crystal X-ray analyses of the synthetically derived samples of compounds 1 and 2 are reported.

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Convergent total syntheses of the amaryllidaceae alkaloids lycoranine A, lycoranine B, and 2-methoxypratosine

Abstract

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