Total syntheses of (+/-)-preussomerins G and I.
[formula: see text] Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.
Chi
S
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Department of Chemistry, University of California, Berkeley 94720, USA.
Heathcock
C H
CH
D001203:Ascomycota / Q000737:chemistry; D004852:Epoxy Compounds; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D004852:Epoxy Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; C410323:preussomerin G; C410322:preussomerin I