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10.3390/org2030016
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Communication

Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes

by
Takahiro Suzuki
1,*,
Riko Nagahama
2,
Muhammad Aiman Fariz
1,
Yuki Yukutake
2,
Kazutada Ikeuchi
1 and
Keiji Tanino
1
1
Department of Chemistry, Hokkaido University, Sapporo 060-0810, Hokkaido, Japan
2
Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-0810, Hokkaido, Japan
*
Author to whom correspondence should be addressed.
Organics 2021, 2(3), 306-312; https://doi.org/10.3390/org2030016
Submission received: 5 August 2021 / Revised: 23 August 2021 / Accepted: 25 August 2021 / Published: 2 September 2021
(This article belongs to the Special Issue Pericyclic Reactions in Organic Synthesis)
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Abstract

Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.01,5]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report the concise synthesis of highly oxidized allo-cedranes by an intramolecular Diels–Alder reaction using ortho-benzoquinones and demonstrate the biomimetic transformation of allo-cedranes by a retro-Claisen/aldol pathway.
Keywords: biomimetic synthesis; Diels–Alder reaction; illicium sesquiterpene; natural product synthesis; skeletal rearrangement biomimetic synthesis; Diels–Alder reaction; illicium sesquiterpene; natural product synthesis; skeletal rearrangement
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MDPI and ACS Style

Suzuki, T.; Nagahama, R.; Fariz, M.A.; Yukutake, Y.; Ikeuchi, K.; Tanino, K. Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes. Organics 2021, 2, 306-312. https://doi.org/10.3390/org2030016

AMA Style

Suzuki T, Nagahama R, Fariz MA, Yukutake Y, Ikeuchi K, Tanino K. Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes. Organics. 2021; 2(3):306-312. https://doi.org/10.3390/org2030016

Chicago/Turabian Style

Suzuki, Takahiro, Riko Nagahama, Muhammad Aiman Fariz, Yuki Yukutake, Kazutada Ikeuchi, and Keiji Tanino. 2021. "Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes" Organics 2, no. 3: 306-312. https://doi.org/10.3390/org2030016

APA Style

Suzuki, T., Nagahama, R., Fariz, M. A., Yukutake, Y., Ikeuchi, K., & Tanino, K. (2021). Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes. Organics, 2(3), 306-312. https://doi.org/10.3390/org2030016

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