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J Org Chem. 2017 Apr 21;82(8):4336-4341. doi: 10.1021/acs.joc.7b00340. Epub 2017 Mar 31.

A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework.

Author information

1
Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.

Abstract

A total synthesis of the racemic modification, (±)-2, of the tazettine-type alkaloid 3-O-demethylmacronine is described. The key steps are an intramolecular Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that embodies the haemanthidine alkaloid framework.

PMID:
28304168
DOI:
10.1021/acs.joc.7b00340

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