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Total Synthesis of the Antifungal Natural Product Mollisin
Author(s) -
Schwolow Sonja,
Kunz Horst,
Rheinheimer Joachim,
Opatz Till
Publication year - 2013
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/ejoc.201301088
Subject(s) - polyketide , total synthesis , chemistry , natural product , moiety , antifungal , pyrone , secondary metabolite , yield (engineering) , stereochemistry , metabolite , fungicide , fungus , organic chemistry , botany , biosynthesis , microbiology and biotechnology , biochemistry , enzyme , biology , materials science , gene , metallurgy
Mollisin, a bioactive polyketide secondary metabolite of the fungus Mollisia caesia , was synthesized in nine linear steps from commercially available 2,6‐dimethyl‐γ‐pyrone. A key transformation in this first total synthesis of mollisin was the ipso substitution of an arylstannane, which permitted the otherwise cumbersome introduction of the characteristic dichloroacetyl moiety. The fungal fungicide was obtained in an overall yield of 9 %.