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Chemical Transformations of the Fungal Meroterpenoid Dhilirolide A Reveal Skeletal Degradation and Rearrangement Reactions with Biosynthetic Implications.
- Source :
-
Organic Letters . Sep2017, Vol. 19 Issue 17, p4488-4491. 4p. - Publication Year :
- 2017
-
Abstract
- Treatment of the fungal meroterpenoid dhilirolide A (1) with either sodium azide or perchloric acid results in conversion of the dhilirane carbon skeleton of 1 to the 14,15-dinordhilirane carbon skeleton of the products 5-7, with and without concomitant transfer of an acetyl residue to form a C-9 acetate ester. The discovery of these transformations, which are vinylogous retro-Claisen-type condensations, suggests an efficient biogenetic route to 14,15-dinordhiliranes such as dhilirolide K (3). [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 19
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 124966636
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b02037