Naturally occurring cyclohexene oxides

Thebtaranonth, C.; Thebtaranonth, Yodhathai

doi:10.1021/ar00123a004

Cited by 55 publications

(26 citation statements)

References 43 publications

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“…The Uvaria species belongs to the Annonaceae and is an important source of natural products with various structures. Previous phytochemical studies on the genus Uvaria have resulted in the isolation of about 30 polyoxygenated cyclohexenes, [1][2][3][4] and some of them have shown interesting antitumorial 1) and antimalarial 2) activities. In the course of our recent phytochemical investigation into the leaves of the Chinese tree, U. purpurea, we isolated four new compounds, 2-O-acetyl-6-O-methylzeylenol (2), 2-O-benzoyl-3-O-debenzoylzeylenone (5), 3-O-debenzoylzeylenone (6) and 3-O-debenzoylgrandi‰orone (8).…”

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confidence: 99%

Polyoxygenated Cyclohexenes from the Chinese Tree,Uvaria Purpurea

Takeuchi

Shi

Sugiyama

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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confidence: 99%

Polyoxygenated Cyclohexenes from the Chinese Tree,Uvaria Purpurea

Takeuchi

Shi

Sugiyama

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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“…On the other hand, a large number of highly oxygenated cyclohexane and cyclohexene derivatives, closely related to carbasugars, have been isolated from nature. Among them were epoxides [62,63] such as cyclophellitol (isolated from Phellinus sp.) [64][65][66][67][68] (5, Figure 3), cyclohexene derivatives such as MK7607 (isolated from Curvularia eragrostidis) [69] (6, Figure 3), streptol (isolated from Streptomyces sp.)…”

Section: Natural Carbapyranosesmentioning

confidence: 99%

Biosynthesis and Biological Activity of Carbasugars

Roscales

Plumet

2016

International Journal of Carbohydrate Chemistry

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The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland's group. Seven years later, the first true natural carbasugar (5a-carba-R-D-galactopyranose) was isolated from a fermentation broth of Streptomyces sp. MA-4145. In the following decades, the chemistry and biology of carbasugars have been extensively studied. Most of these compounds show interesting biological properties, especially enzymatic inhibitory activities, and, in consequence, an important number of analogues have also been prepared in the search for improved biological activities. The aim of this review is to give coverage on the progress made in two important aspects of these compounds: the elucidation of their biosynthesis and the consideration of their biological properties, including the extensively studied carbapyranoses as well as the much less studied carbafuranoses.

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“…After emerging reviews in the 80s [1] and 90s [2] dedicated to cyclohexene epoxides and related compounds, Marco-Contelles and co-workers wrote an extensive and comprehensive apropos review [3]. Biologists and pharmacologists are very interested in them due to their many and varied biological properties.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Natural Epoxyquinoids

Pandolfi

Schapiro²,

Heguaburu³

et al. 2013

COS

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Natural products play an important role as a source not only of potential therapeutic drugs but also of starting materials for semisynthetic new medicines. The epoxyquinoid family, composed by cyclohexane epoxides and related structures, exhibit these characteristics without doubt.Since 2004, significant efforts have been devoted to the stereocontrolled synthesis of these molecules with different and interesting strategies. More than 50 works on this field have been published during this period of time. In addition, many of these polyoxygenated cyclohexenoids exhibit diverse and impressive bioactive shapes. This review aims to analyze the recent advances in the enantioselective processes that have been performed for the total syntheses of these target molecules. It includes a wide range of methodologies for the introduction of chirality either enzymatic or chemical ones. This summarizes microbial preparation of starting materials, lipase kinetic resolutions, use of compounds from the chiral pool, use of chiral auxiliaries and asymmetric catalysis. In a special section, syntheses of scyphostatin are also included.

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Naturally occurring cyclohexene oxides

Cited by 55 publications

References 43 publications

Polyoxygenated Cyclohexenes from the Chinese Tree,Uvaria Purpurea

Polyoxygenated Cyclohexenes from the Chinese Tree,Uvaria Purpurea

Biosynthesis and Biological Activity of Carbasugars

Enantioselective Synthesis of Natural Epoxyquinoids

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