Total synthesis of the tremorgenic indole diterpene paspalinine

Masaru Enomoto; Akira Morita; Shigefumi Kuwahara

doi:10.1002/anie.201206299

Total synthesis of the tremorgenic indole diterpene paspalinine

Masaru Enomoto, Akira Morita, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

38 Citations (Scopus)

Abstract

Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a Pd^II-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement.

Original language	English
Pages (from-to)	12833-12836
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	51
DOIs	https://doi.org/10.1002/anie.201206299
Publication status	Published - 2012 Dec 14

Keywords

alkaloids
natural products
palladium
paspalinine
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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AU - Morita, Akira

AU - Kuwahara, Shigefumi

PY - 2012/12/14

Y1 - 2012/12/14

N2 - Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a PdII-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement.

AB - Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a PdII-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement.

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KW - natural products

KW - palladium

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KW - total synthesis

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ER -

Total synthesis of the tremorgenic indole diterpene paspalinine

Abstract

Keywords

ASJC Scopus subject areas

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