Involvement of Diels-Alder reactions in the biosynthesis of secondary natural products: the late stage of the biosynthesis of the phytotoxins solanapyrones

Advanced intermediates, prosolanapyrones I (6) and II (7) have been synthesized in deuterium labelled form and administered to cultures of Alternaria solani. Incorporation of [17,17,18,18,18-H-2(5)] prosolanapyrone I (6b) afforded solanapyrones A (1) labelled at C-17 and C-18 with the expected integ...

Full description

Saved in:
Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 9; pp. 1225 - 1232
Main Authors Oikawa, H, Suzuki, Y, Katayama, K, Naya, A, Sakano, C, Ichihara, A
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
(-)-SOLANAPYRONE-A
ALBA CELL-CULTURES
ABSOLUTE-CONFIGURATION
ALTERNARIA-SOLANI
PRECURSORS
Online AccessGet full text

Cover

More Information
Summary:Advanced intermediates, prosolanapyrones I (6) and II (7) have been synthesized in deuterium labelled form and administered to cultures of Alternaria solani. Incorporation of [17,17,18,18,18-H-2(5)] prosolanapyrone I (6b) afforded solanapyrones A (1) labelled at C-17 and C-18 with the expected integration in its H-2 NMR spectrum. Subsequently, [2,3,17,18,18,1 8-H-2(6)] prosolanapyrone II(7a) was incorporated into solanapyrone A labelled, as expected, at C-2, C-3, C-17 and C-18. These results strongly support the involvement of a Diels-Alder reaction in the biosynthesis of solanapyrones. This is the first example of intact incorporation of diene-dienophile precursors into natural [4 + 2] adducts.
ISSN:0300-922X
1364-5463
DOI:10.1039/a807704e