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Cyclization of (−)‐Pregaliellalactone in the Fungus Galiella rufa
Author(s) -
Johansson Martin,
Köpcke Bärbel,
Anke Heidrun,
Sterner Olov
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020617)41:12<2158::aid-anie2158>3.0.co;2-p
Subject(s) - fungus , biology , botany
An intramolecular Diels–Alder reaction with inverse electron demand in a polyketide biosynthetic pathway is reported in which the rate of the cyclization is enhanced in vivo. Alive mycelia of the fungus Galiella rufa catalyze the cyclization of (−)‐pregaliellalactone ( 1 ) to (+)‐desoxygaliellalactone ( 2 ), while dead mycelia have no effect. No rate increase was observed with the unnatural enantiomer (+)‐ 1 .