Asymmetric total synthesis of (+)-bermudenynol, a C15 Laurencia metabolite with a vinyl chloride containing oxocene skeleton, through intramolecular amide enolate alkylation.
A substrate-controlled asymmetric total synthesis of (+)-bermudenynol, a compact and synthetically challenging C15 Laurencia metabolite that contains several halogen atoms, is reported. The oxocene core, which contains a vinyl chloride, was constructed by an efficient and highly stereoselective intramolecular amide enolate alkylation (IAEA). This result showcases the broad utility of the IAEA methodology as a useful alternative for cases in which the ring-closing metathesis is inefficient.
College of Pharmacy, Seoul National University, Seoul 151-742 (Korea).
Gyudong
G
Kim
Te-Ik
TI
Sohn
Deukjoon
D
Kim
Robert S
RS
Paton
D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D035964:Oxocins
intramolecular amide enolate alkylation; natural products; oxocenes; total synthesis