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Keywords = α,β-unsaturated δ-lactone

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10 pages, 3714 KB  
Article
Catalyst-Controlled Selectivity Switch in Three-Component Reaction: An NHC-Catalyzed Strategy for the Synthesis of δ-Lactone-Fused Spirobenzofuran-3-ones
by Zhanyong Wang, Ting Yang, Dongfang Liu, Rongxiang Chen, Nan Wang, Hong Liu, Jiarong Li, Kaikai Wang and Hongxin Liu
Molecules 2022, 27(18), 5952; https://doi.org/10.3390/molecules27185952 - 13 Sep 2022
Cited by 3 | Viewed by 2760
Abstract
An efficient, three-component reaction of aldehydes and benzofuran-3-ones was developed. This process provides a new approach for the preparation of synthetically and biologically important spirobenzofuran-3-one derivatives with moderate-to-good yields under mild conditions. A switch of intramolecular to intermolecular domino Michael–aldol–lactonization leading to differential [...] Read more.
An efficient, three-component reaction of aldehydes and benzofuran-3-ones was developed. This process provides a new approach for the preparation of synthetically and biologically important spirobenzofuran-3-one derivatives with moderate-to-good yields under mild conditions. A switch of intramolecular to intermolecular domino Michael–aldol–lactonization leading to differential product formation was achieved by different NHCs catalysis. Full article
(This article belongs to the Special Issue Recent Progress in Synthesis and Bioactivity Studies of Heterocyclic Compounds)
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8 pages, 1466 KB  
Article
Cytotoxic Polyketides with an Oxygen-Bridged Cyclooctadiene Core Skeleton from the Mangrove Endophytic Fungus Phomosis sp. A818
by Wei Zhang, Baobing Zhao, Liangcheng Du and Yuemao Shen
Molecules 2017, 22(9), 1547; https://doi.org/10.3390/molecules22091547 - 14 Sep 2017
Cited by 4 | Viewed by 4812
Abstract
Plant endophytic microorganisms represent a largely untapped resource for new bioactive natural products. Eight polyketide natural products were isolated from a mangrove endophytic fungus Phomosis sp. A818. The structural elucidation of these compounds revealed that they share a distinct feature in their chemical [...] Read more.
Plant endophytic microorganisms represent a largely untapped resource for new bioactive natural products. Eight polyketide natural products were isolated from a mangrove endophytic fungus Phomosis sp. A818. The structural elucidation of these compounds revealed that they share a distinct feature in their chemical structures, an oxygen-bridged cyclooctadiene core skeleton. The study on their structure–activity relationship showed that the α,β-unsaturated δ-lactone moiety, as exemplified in compounds 1 and 2, was critical to the cytotoxic activity of these compounds. In addition, compound 4 might be a potential agonist of AMPK (5′-adenosine monophosphate-activated protein kinase). Full article
(This article belongs to the Special Issue Special Issue in Honor of Professor Thomas James Simpson on the Occasion of His 70th Birthday)
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6 pages, 42 KB  
Communication
Comparative Chemical Analysis of the Essential Oil Constituents in the Bark, Heartwood and Fruits of Cryptocarya massoy (Oken) Kosterm. (Lauraceae) from Papua New Guinea
by Topul Rali, Stewart W. Wossa and David N. Leach
Molecules 2007, 12(2), 149-154; https://doi.org/10.3390/12020149 - 5 Feb 2007
Cited by 66 | Viewed by 14818
Abstract
Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils [...] Read more.
Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-2-one) and C-12 (5,6-dihydro-6-heptyl-2H-pyran-2-one) massoia lactones, while the major fruit oil constituent was benzyl benzoate (68.3 %). The heartwood also contained trace amounts of the C-14 (5,6-dihydro-6-nonyl-2H-pyran-2-one) massoia lactone (1.4 %) and the saturated C-10 derivative d-decalactone (2.5 %). Full article
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