Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula

Sheldrake, Helen M.; Jamieson, Craig; Pascu, Sofia I.; Burton, Jonathan W.

doi:10.1039/b814953d

Cited by 37 publications

(26 citation statements)

References 97 publications

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“…The structure of elatenyne (735) attracted the attention of many research groups, who, utilizing chemical and computational methods, finally succeeded in synthesizing the molecule corresponding to the spectroscopic data of the natural product, and revising the proposed structure to that of a 2,2 0 -bis-tetrahydrofuran derivative. However, the absolute stereochemistry is still unknown [221, 613,[615][616][617][618]. A similar revision was made to the structure of laurendecumbenyne B (733), which was established only on the basis of comparison of NMR data with those originally assigned for 735 [612].…”

Section: Acetogeninsmentioning

confidence: 99%

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The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

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Nature, the most prolific source of biological and chemical diversity, has provided mankind with treatments for health problems since ancient times and continues to be the most promising reservoir of bioactive chemicals for the development of modern drugs. In addition to the terrestrial organisms that still remain a promising source of new bioactive metabolites, the marine environment, covering approximately 70% of the Earth's surface and containing a largely unexplored biodiversity, offers an enormous resource for the discovery of novel compounds. According to the MarinLit database, more than 27,000 metabolites from marine macro- and microorganisms have been isolated to date providing material and key structures for the development of new products in the pharmaceutical, food, cosmeceutical, chemical, and agrochemical sectors. Algae, which thrive in the euphotic zone, were among the first marine organisms that were investigated as sources of food, nutritional supplements, soil fertilizers, and bioactive metabolites.Red algae of the genus Laurencia are accepted unanimously as one of the richest sources of new secondary metabolites. Their cosmopolitan distribution, along with the chemical variation influenced to a significant degree by environmental and genetic factors, have resulted in an endless parade of metabolites, often featuring multiple halogenation sites.The present contribution, covering the literature until August 2015, offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. Since mollusks feeding on Laurencia are, in many cases, bioaccumulating, and utilize algal metabolites as chemical weaponry against natural enemies, metabolites of postulated dietary origin of sea hares that feed on Laurencia species are also included in the present review. Altogether, 1047 secondary metabolites, often featuring new carbocyclic skeletons, have been included.The chapter addresses: (1) the "Laurencia complex", the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; (2) the secondary metabolites, which are organized according to their chemical structures and are classified into sesquiterpenes, diterpenes, triterpenes, acetogenins, indoles, aromatic compounds, steroids, and miscellaneous compounds, as well as their sources of isolation which are depicted in tabulated form, and (3) the biological activity organized according to the biological target and the ecological functions of Laurencia metabolites.

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Section: Acetogeninsmentioning

confidence: 99%

“…Diterpenes belonging to the group of the prevezanes and neorogiolanes (616)(617)(618)(619)(620)(621)(622)(623) feature three rare carbon frameworks that so far are found exclusively in species of Laurencia. To date, eight diterpenes featuring these skeletons have been reported.…”

Section: Prevezanes and Neorogiolanesmentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

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“…Finally, treatment with TMSBr released the free amine 10 without affecting the acid-sensitive acetal functionality. 15 …”

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confidence: 99%

Synthesis of Pandamarilactone-1

et al. 2014

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“…[50] Very recently, a synthesis of 12 was described starting from the ethyl ester analogue of 3c, which was, in turn, synthesized from d-(-)tartrate by using an olefination reaction. [51] Nitromethyl-substituted bislactone 14 was obtained by twofold addition of nitromethane to 3c and subsequent cleavage of acetal 13 (Scheme 7).…”

Section: Functionalization Of 3c With Conservation Of C 2 Symmetrymentioning

confidence: 99%

A Cross‐Metathesis–Conjugate Addition Route to Enantiopure γ‐Butyrolactams and γ‐Lactones from a C₂‐Symmetric Precursor

et al. 2011

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Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula

Cited by 37 publications

References 97 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Synthesis of Pandamarilactone-1

A Cross‐Metathesis–Conjugate Addition Route to Enantiopure γ‐Butyrolactams and γ‐Lactones from a C₂‐Symmetric Precursor

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Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula

Cited by 37 publications

References 97 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Synthesis of Pandamarilactone-1

A Cross‐Metathesis–Conjugate Addition Route to Enantiopure γ‐Butyrolactams and γ‐Lactones from a C2‐Symmetric Precursor

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Product

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A Cross‐Metathesis–Conjugate Addition Route to Enantiopure γ‐Butyrolactams and γ‐Lactones from a C₂‐Symmetric Precursor