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The First Syntheses of (±)‐SDEF 678 Metabolite and (±)‐Speciosins A–C
Author(s) -
Hookins Daniel R.,
Burns Alan R.,
Taylor Richard J. K.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001402
Subject(s) - chemistry , metabolite , benzoquinone , stereochemistry , palladium , total synthesis , halogen , sequence (biology) , organic chemistry , catalysis , biochemistry , alkyl
The epoxyquinone natural products SDEF 678 metabolite, speciosin A, speciosin B and speciosin C have been prepared for the first time via a short synthetic route based around the palladium‐catalysed coupling of a halogen‐substituted 1,4‐benzoquinone monoketal, a Diels–Alder/retro‐Diels–Alder sequence and a diastereoselective epoxidation process.
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