Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA019438
PROPERTIES
| NPAID | NPA019438 |
|---|---|
| CLUSTER ID | 530 |
| NODE ID | 419 |
| NAME | Tanikolide |
| FORMULA | C17H32O3 |
| MOLECULAR WEIGHT (Da) | 284.4400 |
| ACCURATE MASS (Da) | 284.2351 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Lyngbya |
| ORIGIN SPECIES | majuscula |
| InChIKey | NLAYXWYCDWDTBF-QGZVFWFLSA-N |
| InChI | InChI=1S/C17H32O3/c1-2-3-4-5-6-7-8-9-10-13-17(15-18)14-11-12-16(19)20-17/h18H,2-15H2,1H3/t17-/m1/s1 |
| SMILES | CCCCCCCCCCC[C@@]1(CCCC(=O)O1)CO |
ORIGINAL ISOLATION REFERENCE
| CITATION | Singh, Inder Pal; Milligan, Kenneth E.; Gerwick, William H. Tanikolide, a toxic and antifungal lactone from the marine cyanobacterium Lyngbya majuscula Journal of Natural Products 1999 62 (9) 1333-1335. | ||
|---|---|---|---|
| DOI | 10.1021/np990162c | PMID | 10514329 |
SYNTHESES
| CITATION 1 | Fujioka H; Matsuda S; Horai M; Fujii E; Morishita M; Nishiguchi N; Hata K; Kita Y Facile and efficient synthesis of lactols by a domino reaction of 2,3-epoxy alcohols with a hypervalent iodine(III) reagent and its application to the synthesis of lactones and the asymmetric synthesis of (+)-tanikolide. Chemistry - A European Journal 2007 13 (18) 5238-5248. DOI: 10.1002/chem.200601341 PMID: 17385198 | ||
|---|---|---|---|
| CITATION 2 | Gourdet B; Lam HW Catalytic asymmetric dihydroxylation of enamides and application to the total synthesis of (+)-tanikolide. Angewandte Chemie International Edition 2010 49 (46) 8733-8737. DOI: 10.1002/anie.201004328 PMID: 20886496 | ||
| CITATION 3 | Xie Y; Sun M; Zhou H; Cao Q; Gao K; Niu C; Yang H Enantiospecific total synthesis of (+)-tanikolide via a key [2,3]-Meisenheimer rearrangement with an allylic amine N-oxide-directed epoxidation and a one-pot trichloroisocyanuric acid N-debenzylation and N-chlorination. Journal of Organic Chemistry 2013 78 (20) 10251-10263. DOI: 10.1021/jo4016437 PMID: 24053434 | ||
| CITATION 4 | Schomaker JM; Borhan B Total synthesis of (+)-tanikolide via oxidative lactonization. Organic & Biomolecular Chemistry 2004 2 (4) 621-624. DOI: 10.1039/b311432e PMID: 14770242 | ||
| CITATION 5 | Krauss J Total synthesis of (+/-) tanikolide. Natural Product Letters 2001 15 (6) 393-399. DOI: 10.1080/10575630108041309 PMID: 11838977 | ||
