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Synthesis and Absolute Configuration of Hongoquercin A, an Antibacterial Sesquiterpene‐Substituted Orsellinic Acid Isolated as a Fungal Metabolite
Author(s) -
Tsujimori Hisayuki,
Bando Masahiko,
Mori Kenji
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200001)2000:2<297::aid-ejoc297>3.0.co;2-b
Subject(s) - chemistry , metabolite , absolute configuration , sesquiterpene , stereochemistry , antibacterial activity , organic chemistry , bacteria , biochemistry , biology , genetics
(±)‐Hongoquercin A ( 1 ), the racemate of an antibacterial fungal metabolite, has been synthesized starting from geranylacetone ( 2 ) and ethyl orsellinate (ethyl 2,4‐dihydroxy‐6‐methylbenzoate, 5 ). The structure (±)‐ 1 has been confirmed by X‐ray analysis of its ethyl ester (±)‐ 10 . Synthesis of the naturally occurring (+)‐hongoquercin A from (−)‐sclareol ( 11 ) established its configuration as depicted in 1 .