Synthesis of helianane, an unusual marine sesquiterpene employing ring-expansion by flash vacuum thermolysis

Sabui, Subir K.; Venkateswaran, Ramanathapuram V.

doi:10.1016/j.tetlet.2004.10.101

Cited by 25 publications

(12 citation statements)

References 5 publications

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“…Of 38 molecules, one molecule, 10a , was revised to 10b by total synthesis [49,50,51,52]. The structure of 15a was corrected to 15b after total synthesis [53,54,55,56,57]. Hirsutanol C ( 33a ) was revised to 33b by the work of a fungal metabolite [58].…”

Section: New Mnps Discovered From Indonesian Waters In the Period mentioning

confidence: 99%

Marine Natural Products from Indonesian Waters

et al. 2019

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Natural products are primal and have been a driver in the evolution of organic chemistry and ultimately in science. The chemical structures obtained from marine organisms are diverse, reflecting biodiversity of genes, species and ecosystems. Biodiversity is an extraordinary feature of life and provides benefits to humanity while promoting the importance of environment conservation. This review covers the literature on marine natural products (MNPs) discovered in Indonesian waters published from January 1970 to December 2017, and includes 732 original MNPs, 4 structures isolated for the first time but known to be synthetic entities, 34 structural revisions, 9 artifacts, and 4 proposed MNPs. Indonesian MNPs were found in 270 papers from 94 species, 106 genera, 64 families, 32 orders, 14 classes, 10 phyla, and 5 kingdoms. The emphasis is placed on the structures of organic molecules (original and revised), relevant biological activities, structure elucidation, chemical ecology aspects, biosynthesis, and bioorganic studies. Through the synthesis of past and future data, huge and partly undescribed biodiversity of marine tropical invertebrates and their importance for crucial societal benefits should greatly be appreciated.

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Section: New Mnps Discovered From Indonesian Waters In the Period mentioning

confidence: 99%

Marine Natural Products from Indonesian Waters

et al. 2019

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“…446 Helianane, isolated from Haliclona fascigera, 447 was synthesised employing a vacuum thermolytic ring expansion step. 448 A Kenyan Raspailia species gave two purine alkaloid-derivatised diterpenes asmarines G 384 and H 385 and the diterpenoid barekol 386, together with several related known compounds. 449 A Raspailia species (Madagascar) produced further asmarines, I-K 387-389, and the diterpenoid nosyberkol 390.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2006

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This review covers the literature published in 2004 for marine natural products, with 693 citations (491 for the period January to December 2004) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates and echinoderms. The emphasis is on new compounds (716 for 2004), together with their relevant biological activities, source organisms and country of origin. Biosynthetic studies (8), and syntheses (80), including those that lead to the revision of structures or stereochemistries, have been included.

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“…Thus, heating of the TCI derivatives 15 ‐ exo or 16 ‐ exo furnished the cyclobutenes 19 or 20 as the sole products in yields exceeding 70 %, whatever the nature of the protecting group 20. These results have important implications: (1) they lend support to the mechanisms claimed in Figure 2; (2) the stability of the fused cyclobutene has been ascertained21 and (3) a stereoselective synthesis of 12 ‐ exo is mandatory for access to 1 in a practical way.…”

Section: Resultsmentioning

confidence: 54%

Preparation of Conformationally Constrained α₂‐Antagonists: The Bicyclo[3.2.0]heptane Approach

2005

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The aim of this research was to discover α 2 -receptor antagonist subtypes that are more selective than known compounds. We focused on rigid molecules possessing a benzofused bicyclo[3.2.0]heptane skeleton. The synthetic route used relied upon the intramolecular [2+2] cycloaddition of styrylketene precursors. The cycloaddition was remarkably efficient and delivered multigram quantities of the cycloadduct 2. Studies of the removal of the ketone group in 2 revealed a facile opening of the four-membered ring. Upon thermal elimination of TCI-13-endo (TCI = thiocarbonylimidazole) and TCI-13-exo, different products were obtained depending on the stereochemistry of the OH function of the precursor. Distinct mechanisms were proposed to account for

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Synthesis of helianane, an unusual marine sesquiterpene employing ring-expansion by flash vacuum thermolysis

Cited by 25 publications

References 5 publications

Marine Natural Products from Indonesian Waters

Marine Natural Products from Indonesian Waters

Marine natural products

Preparation of Conformationally Constrained α₂‐Antagonists: The Bicyclo[3.2.0]heptane Approach

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Synthesis of helianane, an unusual marine sesquiterpene employing ring-expansion by flash vacuum thermolysis

Cited by 25 publications

References 5 publications

Marine Natural Products from Indonesian Waters

Marine Natural Products from Indonesian Waters

Marine natural products

Preparation of Conformationally Constrained α2‐Antagonists: The Bicyclo[3.2.0]heptane Approach

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Product

Resources

About

Preparation of Conformationally Constrained α₂‐Antagonists: The Bicyclo[3.2.0]heptane Approach