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New Synthesis of (±)‐5‐hydroxymarmesin, biogenetic precursor of the skin photosensitizing agent bergapten (5‐MOP)
Author(s) -
Rodighiero P.,
Manzini P.,
Pastorini G.,
Guiotto A.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180301
Subject(s) - chemistry , coumarin , bergapten , derivative (finance) , stereochemistry , combinatorial chemistry , psoralen , organic chemistry , biochemistry , dna , financial economics , economics
A convenient synthesis is described of (±)‐5‐hydroxymarmesin, 4‐hydroxy‐2‐(1‐hydroxy‐1‐methylethyl)‐2,3‐dihydro‐7 H ‐furo[3,2‐ g ][1]benzopyran‐7‐one, a physiological intermediate in the biogenetic pathway of 5‐O‐alkylfurocoumarins. The synthesis was achieved by a regiospecific 6‐C isoprenylation of 5,7‐diacetoxy‐coumarin; the 6‐C isoprenylated derivative is then submitted to an oxidative cyclization obtaining mainly the title compound together with its angular isomer.