2014 journal article
Studies toward the Total Synthesis of Dihydrolycolucine. Preparation of AB and CEF Ring Fragments
JOURNAL OF ORGANIC CHEMISTRY, 79(12), 5740–5745.
MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Lycopodium / chemistry; Molecular Structure; Pyridinium Compounds / chemistry; Quinolines / chemical synthesis; Quinolines / chemistry; Stereoisomerism
TL;DR:
A strategy for the synthesis of the lycopodium alkaloid dihydrolycolucine was investigated and key reactions include IMDA cycloadditions and retro-Mannich ring-openings to form both the AB and the EF ring fragments.
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(Web of Science)
Source: Web Of Science
Added: August 6, 2018
A strategy for the synthesis of the lycopodium alkaloid dihydrolycolucine (1) has been investigated. Synthetic routes were developed based on N-acylpyridinium salt chemistry to prepare target fragments 3 and 4 that could ultimately converge to the natural product. Key reactions include IMDA cycloadditions and retro-Mannich ring-openings to form both the AB and the EF ring fragments. The ring C precursor was prepared using pyridine substitution and directed lithiation chemistry. A Suzuki cross-coupling of rings C and EF led to the CEF ring fragment. Initial attempts at closure of the seven-membered D ring were unsuccessful.