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J Org Chem DOI:10.1021/jo500878v

Studies toward the total synthesis of dihydrolycolucine. Preparation of AB and CEF ring fragments.

Publication TypeJournal Article
Year of Publication2014
AuthorsCash, BM, Prevost, N, Wagner, FF, Comins, DL
JournalJ Org Chem
Volume79
Issue12
Pages5740-5
Date Published2014 Jun 20
ISSN1520-6904
KeywordsAlkaloids, Lycopodium, Molecular Structure, Pyridinium Compounds, Quinolines, Stereoisomerism
Abstract

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.

DOI10.1021/jo500878v
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/24841361?dopt=Abstract

Alternate JournalJ. Org. Chem.
PubMed ID24841361
PubMed Central IDPMC4066915
Grant ListR01 GM034442 / GM / NIGMS NIH HHS / United States
GM 34442 / GM / NIGMS NIH HHS / United States