14858-07-2Relevant articles and documents
Discoveries and Challenges en Route to Swinhoeisterol A
Duecker, Fenja L.,Heinze, Robert C.,Steinhauer, Simon,Heretsch, Philipp
, p. 9971 - 9981 (2020)
In this work, a full account of the authors’ synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo-steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo-steroids, and periconiastone A, a 13(14→8)abeo-4,14-cyclo-steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed strategies and tactics towards swinhoeisterol A, the successful route that also allowed an access to structurally closely related analogues, such as Δ22-24-epi-swinhoeisterol A, is eventually presented.
Synthesis of the Alleged Structures of Fortisterol and Herbarulide and Structural Revision of Herbarulide
Duecker, Fenja L.,Heinze, Robert C.,Heretsch, Philipp,Mueller, Mira,Zhang, Sudong
supporting information, (2020/02/13)
The alleged structures of 5,6-epoxy-5,6-secosteroids fortisterol and herbarulide differ only in the stereoconfiguration of C24. Applying insights into the hypothetical biosynthesis of this class of natural products, we devised a short synthetic access (four and eight steps, respectively) starting from commercial ergosterol and featuring an alkoxy radical rearrangement. The comparison of nuclear magnetic resonance spectroscopic data revealed herbarulide having the proposed structure of fortisterol, whereas synthesis of another two diastereomers could not conclusively prove the true structure of fortisterol. Along the way, a high-yielding and scalable access to the infamous Burawoy's ketone not requiring chromium(VI) reagents was developed.
The constituents of Gymnopilus spectabilis
Kusano,Koike,Inoue,Nozoe
, p. 3465 - 3470 (2007/10/02)
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