Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA007727
PROPERTIES
| NPAID | NPA007727 |
|---|---|
| CLUSTER ID | 3418 |
| NODE ID | 2583 |
| NAME | Kendomycin |
| FORMULA | C29H42O6 |
| MOLECULAR WEIGHT (Da) | 486.6490 |
| ACCURATE MASS (Da) | 486.2981 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | violaceoruber |
| InChIKey | HKLDUJXJTQJSEJ-OLXNOMCWSA-N |
| InChI | InChI=1S/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+/t14-,16+,17-,18-,19+,22+,24-,28+,29+/m0/s1 |
| SMILES | C[C@H]\1CC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C3=C(C(=O)C(=C4C3=C[C@@](O4)([C@H](C[C@@H](C/C(=C1)/C)C)C)O)C)O)C)O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Bode, Helge B; Zeeck, Axel Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces Journal of the Chemical Society, Perkin Transactions 1 2000 (3) 323-328. | ||
|---|---|---|---|
| DOI | 10.1039/a908387a | PMID | - |
SYNTHESES
| CITATION 1 | Yuan Y; Men H; Lee C Total synthesis of kendomycin: a macro-C-glycosidation approach. Journal of the American Chemical Society 2004 126 (45) 14720-1. DOI: 10.1021/ja0447154 PMID: 15535687 | ||
|---|---|---|---|
| CITATION 2 | Smith AB; Mesaros EF; Meyer EA Total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis synthetic strategy. Journal of the American Chemical Society 2005 127 (19) 6948-9. DOI: 10.1021/ja051420x PMID: 15884927 | ||
| CITATION 3 | Lowe JT; Panek JS Total synthesis of (-)-kendomycin. Organic Letters 2008 10 (17) 3813-6. DOI: 10.1021/ol801499s PMID: 18698784 | ||
| CITATION 4 | Magauer T; Martin HJ; Mulzer J Total synthesis of the antibiotic kendomycin by macrocyclization using photo-Fries rearrangement and ring-closing metathesis. Angewandte Chemie International Edition 2009 48 (33) 6032-6. DOI: 10.1002/anie.200900522 PMID: 19350596 | ||
| CITATION 5 | Tanaka K; Watanabe M; Ishibashi K; Matsuyama H; Saikawa Y; Nakata M Total synthesis of kendomycin featuring intramolecular Dötz benzannulation. Organic Letters 2010 12 (8) 1700-3. DOI: 10.1021/ol100229f PMID: 20225835 | ||
| CITATION 6 | Hoffmeister L; Persich P; Fürstner A Formal total synthesis of kendomycin by way of alkyne metathesis/gold catalysis. Chemistry - A European Journal 2014 20 (15) 4396-402. DOI: 10.1002/chem.201304580 PMID: 24591211 | ||
| CITATION 7 | Sengoku T; Xu S; Ogura K; Emori Y; Kitada K; Uemura D; Arimoto H Total synthesis of the antibiotic kendomycin: a macrocyclization using the Tsuji-Trost etherification. Angewandte Chemie International Edition 2014 53 (16) 4213-6. DOI: 10.1002/anie.201400305 PMID: 24623596 | ||
| CITATION 8 | Tanaka K; Matsuyama H; Watanabe M; Fujimori Y; Ishibashi K; Ozawa T; Sato T; Saikawa Y; Nakata M Synthesis and biological evaluation of kendomycin and its analogues. Journal of Organic Chemistry 2014 79 (21) 9922-47. DOI: 10.1021/jo5015273 PMID: 25136928 | ||
