Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA002318
PROPERTIES
| NPAID | NPA002318 |
|---|---|
| CLUSTER ID | 1392 |
| NODE ID | 1168 |
| NAME | Varitriol |
| FORMULA | C15H20O5 |
| MOLECULAR WEIGHT (Da) | 280.3200 |
| ACCURATE MASS (Da) | 280.1311 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Emericella |
| ORIGIN SPECIES | variecolor |
| InChIKey | JGUADRHIBCXAFH-MVBSPKBLSA-N |
| InChI | InChI=1S/C15H20O5/c1-9-14(17)15(18)13(20-9)7-6-10-4-3-5-12(19-2)11(10)8-16/h3-7,9,13-18H,8H2,1-2H3/b7-6+/t9-,13+,14-,15+/m1/s1 |
| SMILES | C[C@@H]1[C@H]([C@H]([C@@H](O1)/C=C/C2=C(C(=CC=C2)OC)CO)O)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Malmstrom, Joan; Christophersen, Carsten; Barrero, Alejandro F.; Enrique Oltra; Justicia, Jose; Rosales, Antonio Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor Journal of Natural Products 2002 65 (3) 364-367. | ||
|---|---|---|---|
| DOI | 10.1021/np0103214 | PMID | 11908979 |
SYNTHESES
| CITATION 1 | Sun T; Deutsch C; Krause N Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs. Organic & Biomolecular Chemistry 2012 10 (30) 5965-5970. DOI: 10.1039/c2ob25069a PMID: 22411187 | ||
|---|---|---|---|
| CITATION 2 | Sánchez-Eleuterio A; García-Santos WH; Díaz-Salazar H; Hernández-Rodríguez M; Cordero-Vargas A Stereocontrolled Nucleophilic Addition to Five-Membered Oxocarbenium Ions Directed by the Protecting Groups. Application to the Total Synthesis of (+)-Varitriol and of Two Diastereoisomers Thereof. Journal of Organic Chemistry 2017 82 (16) 8464-8475. DOI: 10.1021/acs.joc.7b01211 PMID: 28742352 | ||
| CITATION 3 | Clemens RT; Jennings MP An efficient total synthesis and absolute configuration determination of varitriol. Chemical Communications 2006 (25) 2720-2721. DOI: 10.1039/b603931f PMID: 16786099 | ||
| CITATION 4 | Kumar V; Shaw AK First total synthesis of (+)-varitriol. Journal of Organic Chemistry 2008 73 (19) 7526-7531. DOI: 10.1021/jo8013534 PMID: 18759478 | ||
| CITATION 5 | Zeng J; Vedachalam S; Xiang S; Liu XW Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol. Organic Letters 2011 13 (1) 42-45. DOI: 10.1021/ol102473k PMID: 21114334 | ||
| CITATION 6 | Sudhakar G; Raghavaiah J Total synthesis of varitriol, varioxirane, and enantiomer of the proposed biosynthetic precursor. Journal of Organic Chemistry 2013 78 (17) 8840-8846. DOI: 10.1021/jo4011766 PMID: 23944735 | ||
| CITATION 7 | Ghosal P; Sharma D; Kumar B; Meena S; Sinha S; Shaw AK Diastereoselective one-pot Wittig olefination-Michael addition and olefin cross metathesis strategy for total synthesis of cytotoxic natural product (+)-varitriol and its higher analogues. Organic & Biomolecular Chemistry 2011 9 (21) 7372-7383. DOI: 10.1039/c1ob06039b PMID: 21897926 | ||
| CITATION 8 | Ghosh S; Pradhan TK Stereoselective total synthesis of (+)-varitriol, (-)-varitriol, 5'-epi-(+)-varitriol, and 4'-epi-(-)-varitriol from D-mannitol. Journal of Organic Chemistry 2010 75 (6) 2107-2110. DOI: 10.1021/jo100001p PMID: 20180524 | ||
