Work

Studies toward the Total Synthesis of Dihydrolycolucine. Preparation of AB and CEF Ring Fragments

Year: 2014

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo500878v

Authors: Brandon M. Cash, Natacha Prevost, Florence F. Wagner, Daniel L. Comins

Institution: North Carolina State University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500