Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes
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.
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2020 ◽
2016 ◽
Vol 20
(22)
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pp. 2421-2442
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2014 ◽
Vol 18
(12)
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pp. 1586-1620
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2018 ◽
Vol 15
(2)
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pp. 221-229
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