Simple Total Syntheses of Biologically Active Pentathiadecane Natural Products, 2,4,5,7,9-Pentathiadecane 2,2,9,9-Tetraoxide (Dysoxysulfone), from Dysoxylum richii, and 2,3,5,7,9-Pentathiadecane 9,9-Dioxide, the Misidentified Lenthionine Precursor SE-3 from Shiitake Mushroom (Lentinus edodes)

Autor:	Mohan Thiruvazhi, Eric Block, Russell Deorazio
Rok vydání:	1994
Předmět:	Mushroom biology Organic Chemistry Total synthesis biology.organism_classification Potassium permanganate chemistry.chemical_compound chemistry Lentinus Organic chemistry Dysoxylum Lenthionine Aliphatic compound Tulbaghia violacea
Zdroj:	The Journal of Organic Chemistry. 59:2273-2275
ISSN:	1520-6904 0022-3263
Popis:	Brief total syntheses are reported for 2,4,5,1,9-pentathiadecane 2,2,9,9-tetraoxide (dysoxysulfone, 1), from the Fijian tree Dysoxylum richii, 2,3,5,1,9-pentathiadecane 9,9-dioxide (8), from shiitake mushroom (Lentinus edodes), and 2,4,5,1-tetrathiaoctane 2,2-dioxide (2a) from Tulbaghia violacea, starting from 1,2,4-trithiolane (d) for 1,1,2,4,6-tetrathiepane (5) for 8, and 2,4,5,1-tetrathiaoctane (9) for 2a and employing regispecific oxidation of intermediate penta- or tetrasulfides using KMnO 4 along with Zn(OAc) 2 or FeCl 3 to prevent product degradation by the base produced during oxidation
Databáze:	OpenAIRE
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