Concise Synthesis of the Terpene Core Structure of Suaveolindole through a Time-Economic Route

Hiroki Tanimoto; Kazuki Tojo; Tsumoru Morimoto; Kiyomi Kakiuchi

doi:10.1055/a-1707-6593

Synlett, Table of Contents

Synlett 2022; 33(03): 273-276
DOI: 10.1055/a-1707-6593

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Concise Synthesis of the Terpene Core Structure of Suaveolindole through a Time-Economic Route

Hiroki Tanimoto ∗

^aDivision of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan

^bFaculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan

,

Kazuki Tojo

^aDivision of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan

,

Tsumoru Morimoto

^aDivision of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan

,

Kiyomi Kakiuchi

^aDivision of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan

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Abstract

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Abstract

The terpene core structure of suaveolindoles was synthesized through a concise route in a time-economical manner. A scalable synthetic route from pulegone delivered the desired α,β,γ,δ-unsaturated ester in a brief period. By way of Eschenmoser–Claisen rearrangement, carbon side-chain moiety at the crowded double-allylic position was introduced stereoselectively.

Key words

terpene - time-economy synthesis - natural product synthesis - Claisen rearrangement - DFT calculation

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References

References and Notes

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