17235-15-3

Upstream product

• 6051-53-2 (E)-4-(2-hydroxyphenyl)but-3-en-2-one 
• 917-54-4 methyllithium 
• 91-64-5 coumarin 
• 74-88-4 methyl iodide 

Downstream Products

• 2513-25-9 2,2-dimethyl-2H-chromene 
• 36852-15-0 4-(2-Hydroxyphenyl)-3-methyl-1,3-butadien 
• 58740-82-2 (3S,4S)-3,4-epoxy-2,2-dimethylchromane 
• 58740-82-2 (3R,4R)-3,4-epoxy-2,2-dimethylchromane 

Relevant academic research and scientific papers

2H-chromenes generated by an iron(III) complex-catalyzed allylic cyclization

A straightforward method based on an iron(III) complex-catalyzed cyclization of 2-(1-hydroxyallyl)phenols is reported to access a large variety of 2H-chromenes. This method was applied to the total synthesis of a natural product, tephrowatsin B.

Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1)

Procaryotic (bacterial) dioxygenase-catalysed asymmetric dihydroxylation of chromene and 2,2-dimethylchromene to yield the (4S)-enantiomers of the corresponding cis-diols exclusively is reported. The epoxide, and derived cis- and trans-diol products from the previously reported eucaryotic (mammalian) metabolism of precocene-1 (7-methoxy-2,2-dimethylchromene), and the corresponding epoxide and diol derivatives of chromene and 2,2-dimethylchromene, have now been obtained in enantiopure form by chemical resolution of the corresponding bromohydrins using methoxy-(trifluoromethyl)phenylacetic acid (MTPA) or camphanate esters. The absolute configurations of the epoxides, cis- and trans-diols have been determined by chemical synthesis from, and stereochemical correlation with, the corresponding camphanate and MTPA esters. X-Ray crystal structure analysis has provided an unequivocal method for assignment of the absolute stereochemistry in each case.