A novel route to the vinyl sulfide nine-membered macrocycle moiety of Griseoviridin.
The synthetic potentialities of cerium(III) chloride are demonstrated by the synthesis of a nine-membered ring heterocycle component of Griseoviridin (3) in optically active form. The key step involves the stereospecific formation of the alpha-carbalkoxy alkenyl sulfide moiety using a combination system of cerium(III) chloride heptahydrate and sodium iodide.
Marcantoni
E
E
Dipartimento di Scienze Chimiche, Camerino (MC), Italy. enricom@camserv.unicam.it
Massaccesi
M
M
Petrini
M
M
Bartoli
G
G
Bellucci
M C
MC
Bosco
M
M
Sambri
L
L
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002563:Cerium / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides; D012974:Sodium Iodide / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D014769:Virginiamycin / Q000138:chemical synthesis* / Q000737:chemistry
D000900:Anti-Bacterial Agents; D006571:Heterocyclic Compounds; D010455:Peptides; D013440:Sulfides; D014769:Virginiamycin; D002563:Cerium; C010583:griseoviridin; D012974:Sodium Iodide; C026690:cerous chloride