86761-68-4

Upstream product

• 1708-29-8 2,5-dihydrofuran 
• 698-16-8 benzohydroximoyl chloride 

Downstream Products

• 119476-25-4 (2,5-dihydrofuran-3-yl)(phenyl)methanone 
• 107317-70-4 trans-3-benzoyl-4-hydroxytetrahydrofuran 
• 107317-70-4 (3RS,4RS)-cis-4-Benzoyl-3-hydroxytetrahydrofuran 
• 147200-46-2 (3R,4R)-4-Benzyl-3-hydroxytetrahydrofuran 
• 147200-51-9 (3S,4S)-4-Benzyl-3-hydroxytetrahydrofuran 
• 86761-70-8 5-Formyl-4-phenyl-2,3-dihydro-6H-1,3-oxazine 
• 96986-28-6 3-phenyl-2,7-dioxa-4-azabicyclo<3,3,0>oct-3-ene 

Relevant academic research and scientific papers

Enantiocontrolled Synthesis of Burseran, Brassilignan, Dehydroxycubebin, and Other Tetrahydrofuran Lignans in Both Enantiomeric Forms. Application of Intermolecular Nitrile Oxide Cycloadditions and Lipase Mediated Kinetic Resolutions

Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach.Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of alcohols 11 by lipase PS.The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99percent ee).This is followed by a SN2 displacement of tosylates 15 and 18 by α-lithiobenzyl phenyl sulfides.In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methoxybenzyl)tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydroxy cubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16percent.

PREPARATION AND PHOTOCHEMISTRY OF FUROISOXAZOLINES. AN EXTRAORDINARILY UNAMBIGUOUS PHOTO-INDUCED REARRANGEMENT

Preparation and photolysis of furoisoxazoline derivatives is described.The respective compounds IVa, II and VI were obtained by a 1,3-dipolar cycloadition of benzenenitrile oxide to 5,6-dimethoxycarbonyl-7-oxabicyclo-2-heptene, 2,5-dihydrofuran and furan; IVb was synthesized from benzoylnitrile oxide.The biradical primarily formed by photolysis was stabilized with respect to the arrangement of the heteroatom and the isoxazoline chromophore.The new 1,3-oxazine derivatives III and V were obtained in high yields as single products.The quantum yield of photoreaction of II, IVa and XXVII was found to be 0.04, 0.26 and 0.07 respectively.Were the stabilization of the radical by conjugation with the lone electron pair of oxygen impossible, oxazoline VII should be formed.Photolysis of the benzoyl derivative IVb had an anomalous course and yielded the β-aminochalcone Xb.