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Chemical and enzymatic synthesis of buprestin A and B—bitter acylglucosides from Australian jewel beetles (Coleoptera: Buprestidae)

Title data

Schramm, Sabine ; Dettner, Konrad ; Unverzagt, Carlo:
Chemical and enzymatic synthesis of buprestin A and B—bitter acylglucosides from Australian jewel beetles (Coleoptera: Buprestidae).
In: Tetrahedron Letters. Vol. 47 (2006) Issue 44 . - pp. 7741-7743.
ISSN 0040-4039
DOI: https://doi.org/10.1016/j.tetlet.2006.08.119

Abstract in another language

A chemical and enzymatic synthesis was developed for buprestin A and B originally isolated from Australian jewel beetles (Coleoptera: Buprestidae). The common motif of both acylglucosides is a β-d-glucopyranose-1,2-bis(pyrrole-2-carboxylate). Starting from 1,3,4,6-tetra-O-acetyl-α-d-glucose, the first pyrrole-2-carboxylate was introduced by DCC–DMAP mediated esterification. After conversion to a trichloroacetimidate the anomeric pyrrole-2-carboxylate was installed. Selective removal of the acetates was accomplished using immobilized Candida antarctica lipase. The resulting triol was converted to Buprestin A or B via a Mitsunobu reaction.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: BAYCEER41007
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Chair Animal Ecology II - Evolutionary Animal Ecology
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors > Chair Animal Ecology II - Univ.-Prof. Dr. Konrad Dettner
Research Institutions > Research Centres > Bayreuth Center of Ecology and Environmental Research- BayCEER
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology
Research Institutions
Research Institutions > Research Centres
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors
Result of work at the UBT: Yes
DDC Subjects: 500 Science
Date Deposited: 29 Jun 2015 06:09
Last Modified: 29 Jun 2015 06:09
URI: https://eref.uni-bayreuth.de/id/eprint/15537