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

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

a   Division of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan
b   Faculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
,
a   Division of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan
,
a   Division of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan
,
Kiyomi Kakiuchi
a   Division of Materials Science Nara, Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan
› Author Affiliations
This work was supported in part by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant C, JP18K05460).


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.

Supporting Information



Publication History

Received: 10 November 2021

Accepted after revision: 26 November 2021

Accepted Manuscript online:
26 November 2021

Article published online:
17 December 2021

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