Hyperdioxane A, a Conjugate of Dibenzo-1,4-dioxane and Sesquiterpene from Hypericum ascyron

Two new dibenzo-1,4-dioxane derivatives, hyperdioxanes A (1) and B (2), were isolated from the roots of a Hypericaceous plant, Hypericum ascyron. Hyperdioxane A (1) is a conjugate of dibenzo-1,4-dioxane and sesquiterpene with an unprecedented heptacyclic ring system. The structures of 1 and 2 were a...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (18), p.5977-5980
Main Authors: Niwa, Kanji, Tanaka, Naonobu, Kim, Sang-Yong, Kojoma, Mareshige, Kashiwada, Yoshiki
Format: Article
Language:English
Subjects:
Dioxanes - chemistry
Hypericum - chemistry
Molecular Conformation
Plant Roots - chemistry
Sesquiterpenes - chemistry
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Summary:Two new dibenzo-1,4-dioxane derivatives, hyperdioxanes A (1) and B (2), were isolated from the roots of a Hypericaceous plant, Hypericum ascyron. Hyperdioxane A (1) is a conjugate of dibenzo-1,4-dioxane and sesquiterpene with an unprecedented heptacyclic ring system. The structures of 1 and 2 were assigned by detailed spectroscopic analyses, including application of a modified Mosher’s method. A possible biogenetic pathway of hyperdioxane A (1) from hyperdioxane B (2) and a sesquiterpene, eremophil-9,11(13)-dien-8β,12-olide (3), is presented.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02739