Studies toward the total synthesis of dihydrolycolucine. Preparation of AB and CEF ring fragments.
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.
Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695-8204, United States.
Brandon M
BM
Cash
Natacha
N
Prevost
Florence F
FF
Wagner
Daniel L
DL
Comins
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D011726:Pyridinium Compounds; D011804:Quinolines; C000593449:dihydrolycolucine