Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA008702
PROPERTIES
| NPAID | NPA008702 |
|---|---|
| CLUSTER ID | 1506 |
| NODE ID | 1238 |
| NAME | Hamigeran B |
| FORMULA | C18H21BrO3 |
| MOLECULAR WEIGHT (Da) | 365.2670 |
| ACCURATE MASS (Da) | 364.0674 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Hamigera |
| ORIGIN SPECIES | tarangaensis |
| InChIKey | LJUSWSWJFIZLDY-AJAPIDPKSA-N |
| InChI | InChI=1S/C18H21BrO3/c1-8(2)10-5-6-18(4)13(10)11-7-9(3)14(19)15(20)12(11)16(21)17(18)22/h7-8,10,13,20H,5-6H2,1-4H3/t10-,13-,18-/m1/s1 |
| SMILES | CC1=C(C(=C2C(=C1)[C@H]3[C@H](CC[C@]3(C(=O)C2=O)C)C(C)C)O)Br |
ORIGINAL ISOLATION REFERENCE
| CITATION | Wellington, Keri D; Cambie, Richard C; Rutledge, Peter S; Bergquist, Patricia R Chemistry of Sponges. 19. Novel Bioactive Metabolites from Hamigera t arangaensis Journal of Natural Products 2000 63 (1) 79-85. | ||
|---|---|---|---|
| DOI | 10.1021/np9903494 | PMID | - |
SYNTHESES
| CITATION 1 | Clive DL; Wang J Stereospecific total synthesis of the antiviral agent hamigeran B--use of large silyl groups to enforce facial selectivity and to suppress hydrogenolysis. Angewandte Chemie International Edition 2003 42 (29) 3406-9. DOI: 10.1002/anie.200351519 PMID: 12888971 | ||
|---|---|---|---|
| CITATION 2 | Trost BM; Pissot-Soldermann C; Chen I; Schroeder GM An asymmetric synthesis of hamigeran B via a Pd asymmetric allylic alkylation for enantiodiscrimination. Journal of the American Chemical Society 2004 126 (14) 4480-1. DOI: 10.1021/ja0497025 PMID: 15070341 | ||
| CITATION 3 | Miesch L; Welsch T; Rietsch V; Miesch M Intramolecular alkynylogous mukaiyama aldol reaction starting from bicyclic alkanones tethered to alkynyl esters: formal total synthesis of (+/-)-hamigeran B. Chemistry - A European Journal 2009 15 (17) 4394-401. DOI: 10.1002/chem.200802309 PMID: 19283820 | ||
| CITATION 4 | Cao BC; Wu GJ; Yu F; He YP; Han FS A Total Synthesis of (-)-Hamigeran B and (-)-4-Bromohamigeran B. Organic Letters 2018 20 (12) 3687-3690. DOI: 10.1021/acs.orglett.8b01490 PMID: 29874089 | ||
