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Secopaxilline A, an indole-diterpenoid derivative from an aciduric Penicillium fungus, its identification and semisynthesis
- Source :
- Organic Chemistry Frontiers. 5:2835-2839
- Publication Year :
- 2018
- Publisher :
- Royal Society of Chemistry (RSC), 2018.
-
Abstract
- Secopaxilline A (1), a new meroditerpenoid derived from indole-diterpenoid by the oxidative cleavage of a carbon–nitrogen bond, was isolated from an aciduric fungus Penicillium camemberti OUCMDZ-1492. Its structure, including absolute configuration, was fully elucidated based on spectroscopic analysis and X-ray single crystal diffraction. Secopaxilline A is the first example of indole-diterpenoid derivatives possessing a carbon–nitrogen bond cleavage skeleton. It was synthesized from paxilline with a 45% overall yield. The one-pot synthesis of the biosynthetic precursor, deacetylsecopaxilline A (4), from paxilline was also developed.
- Subjects :
- Indole test
biology
010405 organic chemistry
Stereochemistry
Organic Chemistry
Absolute configuration
010402 general chemistry
biology.organism_classification
01 natural sciences
Semisynthesis
0104 chemical sciences
chemistry.chemical_compound
chemistry
Penicillium camemberti
Yield (chemistry)
Penicillium
Paxilline
Bond cleavage
Subjects
Details
- ISSN :
- 20524129
- Volume :
- 5
- Database :
- OpenAIRE
- Journal :
- Organic Chemistry Frontiers
- Accession number :
- edsair.doi...........079a825a3efccb7759872ce90e445e09