Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA010400
PROPERTIES
| NPAID | NPA010400 |
|---|---|
| CLUSTER ID | 4161 |
| NODE ID | 2732 |
| NAME | FR182877 |
| FORMULA | C24H32O5 |
| MOLECULAR WEIGHT (Da) | 400.5150 |
| ACCURATE MASS (Da) | 400.2250 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp No. 9885 |
| InChIKey | WMRQHSFWMFGIFW-SUKKNUONSA-N |
| InChI | InChI=1S/C24H32O5/c1-9-7-13-17(21(26)11(3)20(13)25)16-12(9)8-14-18(16)19-22-10(2)15(28-23(19)27)5-6-24(14,4)29-22/h7,10-18,20-21,25-26H,5-6,8H2,1-4H3/t10?,11-,12-,13+,14+,15-,16-,17-,18+,20-,21+,24-/m1/s1 |
| SMILES | CC1=C[C@@H]2[C@H](O)[C@@H](C)[C@H](O)[C@H]2[C@@H]2[C@H]3C4=C5O[C@](C)(CC[C@@H](OC4=O)C5C)[C@H]3C[C@H]12 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Sato, Bunji; Muramatsu, Hideyuki; Miyauchi, Michiyo; Hori, Yasuhiro; Takase, Shigehiro; Hino, Motohiro; Hashimoto, Seiji; Terano, Hiroshi A new antimitotic substance, FR182877. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities Journal of Antibiotics 2000 53 (2) 123-130. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.53.123 | PMID | 10805571 |
SYNTHESES
| CITATION 1 | Evans DA; Starr JT A cascade cycloaddition strategy leading to the total synthesis of (-)-FR182877. Angewandte Chemie International Edition 2002 41 (10) 1787-1790. DOI: 10.1002/1521-3773(20020517)41:10<1787::aid-anie1787>3.0.co;2-v PMID: 19750718 | ||
|---|---|---|---|
| CITATION 2 | Evans DA; Starr JT A cycloaddition cascade approach to the total synthesis of (-)-FR182877. Journal of the American Chemical Society 2003 125 (44) 13531-13540. DOI: 10.1021/ja037643+ PMID: 14583050 | ||
| CITATION 3 | Tanaka N; Suzuki T; Matsumura T; Hosoya Y; Nakada M Total synthesis of (-)-FR182877 through tandem IMDA-IMHDA reactions and stereoselective transition-metal-mediated transformations. Angewandte Chemie International Edition 2009 48 (14) 2580-2583. DOI: 10.1002/anie.200900097 PMID: 19226590 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@H]1[C@H]([C@H]2C=C([C@H]3C[C@H]4[C@@H]([C@H]3[C@@H]2[C@H]1O)C5=C6[C@H]([C@@H](CC[C@]4(O6)C)OC5=O)C)C)O | Sato, Bunji; Muramatsu, Hideyuki; Miyauchi, Michiyo; Hori, Yasuhiro; Takase, Shigehiro; Hino, Motohiro; Hashimoto, Seiji; Terano, Hiroshi A new antimitotic substance, FR182877. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities Journal of Antibiotics 2000 53 (2) 123-130. DOI: 10.7164/antibiotics.53.123 PMID: 10805571 | ||
| 2 | CC1=C[C@@H]2[C@H](O)[C@@H](C)[C@H](O)[C@H]2[C@@H]2[C@H]3C4=C5O[C@](C)(CC[C@@H](OC4=O)C5C)[C@H]3C[C@H]12 | Vosburg, David A; Vanderwal, Christopher D; Sorensen, Erik J A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Journal of the American Chemical Society 2002 124 (17) 4552-3. DOI: 10.1021/ja025885o PMID: 11971689 | ||
