Journal
SYNLETT
Volume -, Issue 4, Pages 639-643Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1219371
Keywords
nemorosone; bridgehead substitution; iodine-lithium exchange; B3LYP calculations
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Funding
- Engineering and Physical Sciences Research Council (EPSRC)
- University of Birmingham
- EPSRC [EP/H013040/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/H013040/1] Funding Source: researchfish
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The synthesis of nemorosone, a polyprenylated acylphloroglucinol isolated from Clusia rosea, was achieved by means of a bridgehead substitution process, involving initial iodination and subsequent lithium-iodine exchange followed by acylation. The difficulties in the bridgehead substitution are discussed, and a probable explanation proposed, based on molecular modelling.
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