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Synthesis of 4,7‐Dihydroxyperhydroisobenzofuran‐1‐one and Comparison with Zwergal's Structure of “garlicin”
Author(s) -
Nour Reema Abdel,
Schneider Karin,
Urban Ernst
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920167
Subject(s) - chemistry , maleic anhydride , lactone , furan , adduct , regioselectivity , catalytic hydrogenation , catalysis , cleavage (geology) , organic chemistry , acetal , medicinal chemistry , polymer chemistry , copolymer , polymer , geotechnical engineering , fracture (geology) , engineering
The Diels‐Alder reaction of 2‐(benzoyloxy)furan ( 2 ) with maleic anhydride leads to the adduct 3 which, on hydrogenation, affords the exo anhydride 4a (71%) and endo anhydride 4b (2.4%). The regioselective reduction of 4a and 4b with NaBH 4 leads to the lactones 5a and 5b , respectively. Base‐catalyzed cleavage of 5a gives the keto lactone 6 or dimethyl acetal 7 , depending on the reaction conditions. Catalytic hydrogenation of keto lactone 6 results in the diastereoselective formation of the title compound 8a which has been converted into the acetate 8b and trifluoroacetate 8c . The structure and properties of the dihydroxylactone 8a are discussed in comparison with garlic compound “garlicin”.