A concise, convergent total synthesis of monocerin.
A concise and convergent eight-step synthesis of the antifungal metabolite monocerin 1 is reported. The key step involves an allylsilane metathesis/aldehyde condensation sequence to establish the core 2,3,5-trisubstituted tetrahydrofuran. End-game approaches based around intramolecular Heck chemistry revealed an interesting example of formal 6-endo cyclisation, the origin of which was probed using model substrates. The synthesis was ultimately completed by a strategy involving stepwise oxidative cleavage of the C3-ethenyl substituent.
Cassidy
John H
JH
Department of Chemistry, Imperial College, London, SW7 2AY, UK.
Farthing
Christopher N
CN
Marsden
Stephen P
SP
Pedersen
Anders
A
Slater
Mark
M
Stemp
Geoffrey
G
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; C485193:monocerin