title: Syntheses of chloroisosulochrin and isosulochrin and biomimetic elaboration to maldoxin, maldoxone, dihydromaldoxin, and dechlorodihydromaldoxin.
abstract: An efficient synthesis of chloroisosulochrin was accomplished using a novel ortho-selective chlorination of a phenol with sulfuryl chloride and 2,2,6,6-tetramethylpiperidine as the key step. Further elaboration by a biomimetic route converted chloroisosulochrin to dihydromaldoxin, maldoxone (lactone formed by dehydration of dihydromaldoxin), and maldoxin and isosulochrin to dechlorodihydromaldoxin and dechloromaldoxin.
authors.affiliation: Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Min
authors.initials: M
authors.lastname: Yu
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider
mesh_terms: D001565:Benzoates / Q000138:chemical synthesis*; D040761:Biomimetic Materials / Q000138:chemical synthesis*; D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis*; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: D001565:Benzoates; D006843:Hydrocarbons, Chlorinated; D007783:Lactones; D013141:Spiro Compounds; C562278:chloroisosulochrin; C562279:maldoxin; C562277:isosulochrin