Relative configuration of the marine natural product elatenyne using NMR spectroscopic and chemical derivatization methodologies

Natural Product Communications

Volumn 8, Issue 6, 2013, Pages 729-732

  Brkljača, Robert ^a   Urban, Sylvia ^a  

^a RMIT UNIVERSITY   (Australia)

Author keywords

"Click" chemistry; Elatenyne; Laurencia elata; Natural products; nOe NMR enhancements; Relative configuration

Indexed keywords

1,2,3 TRIAZOLE [4,4' DIBROMO 5 ETHYL 5' (PENT 2 EN 4 YNYL)OCTAHYDRO[2,2']BIFURAN]; ELATENYNE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CLICK CHEMISTRY; DERIVATIZATION; DIASTEREOISOMER; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS;

LAURENCIA ELATA;

EID: 84886392686     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1300800612     Document Type: Article

References (11)

1. Hall JG, Reiss JA. (1986) Elatenyne - a pyrano[3,2-b]pyranyl vinyl acetylene fom the red alga Laurencia elata. Australian Journal of Chemistry, 39, 1401-1409.
2. Sheldrake HM, Jamieson C, Burton JW. (2006) The changing faces of halogenated marine natural products: Total synthesis of the reported structures of elatenyne and an enyne from Laurencia majuscula. Angewandte Chemie, 45, 7199-7202.
3. Sheldrake HM, Jamieson C, Pascu SI, Burton JW. (2009) Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula. Organic and Biomolecular Chemsitry, 7, 238-252.
4. 13C NMR calculations: Prediction of the stereochemistry of elatenyne. Journal of Organic Chemistry, 73, 4053-4062.
5. Dyson BS, Burton JW, Sohn T-i, Kim B, Bae H, Kim D. (2012) Total synthesis and structure confirmation of elatenyne: Success of computational methods for NMR prediction with highly flexible diastereomers. Journal of the American Chemical Society, 134, 11781-11790.
6. Dias DA, Urban S. (2011) Phytochemical studies of the southern Australian marine alga, Laurencia elata. Phytochemistry, 72, 2081-2089.
7. Kikuchi H, Suzuki T, Kurosawa E, Suzuki M. (1991) The structure of notoryne, a halogenated C15 nonterpenoid with a novel carbon skeleton from the red alga Laurencia nipponica Yamada. Bulletin of the Chemical Society of Japan, 64, 1763-1775.
8. H,H and the reduction of molecular symmetry by simple NMR inverse detection experiments. European Journal of Organic Chemistry, 938-940.
9. Ryan JM. (2008) PhD thesis. Novel secondary metabolites from New Zealand marine sponges. Victoria University of Wellington, Wellington, New Zealand.
10. Binder WH, Sachsenhofer R. (2008) 'Click' chemistry in polymer and material science: An update. Macromolecular Rapid Communications, 29, 952-981.
11. Reddy P, Urban S. (2008) Linear and cyclic C18 terpenoids from the Southern Australian marine brown alga Cystophora moniliformis. Journal of Natural Products, 71, 1441-1446.