Secopaxilline A, an indole-diterpenoid derivative from an aciduric Penicillium fungus, its identification and semisynthesis
Literature Information
Publication Date
2018-08-24
DOI
10.1039/C8QO00756J
Impact Factor
5.281
Authors
Yaqin Fan, Yi Wang, Arthit Chairoungdua, Pawinee Piyachaturawat
View Original
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.
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Organic Chemistry Frontiers
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7.8
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8.7%
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724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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