The Total Synthesis of Heraclemycin B through β-Ketosulfoxide and Aldehyde Annulation

Herein we describe a total synthesis of the natural product heraclemycin B. This synthetic approach follows a Diels–Alder strategy to form the anthracenone core followed by a β‐ketosulfoxide and aldehyde annulation to form the 4‐pyranone D ring. The spectral data for the synthesized product matches...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2015-09, Vol.4 (9), p.936-942
Main Authors: Jones, Kieran D., Rixson, James E., Skelton, Brian W., Gericke, Kersten M., Stewart, Scott G.
Format: Article
Language:English
Subjects:
anthrapyranones
antibacterial
heraclemycin B
total synthesis
β-ketosulfoxides
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Summary:Herein we describe a total synthesis of the natural product heraclemycin B. This synthetic approach follows a Diels–Alder strategy to form the anthracenone core followed by a β‐ketosulfoxide and aldehyde annulation to form the 4‐pyranone D ring. The spectral data for the synthesized product matches that reported in the isolation studies. B side: Herein we describe the total synthesis of the natural product heraclemycin B. The synthetic approach to heraclemycin B follows a β‐ketosulfoxide and aldehyde annulation route to form the 4‐pyranone D ring. A brief study of this annulation is also described.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201500184