Synthesis of porritoxin.
A total synthesis following the sequence in Scheme 1 confirms that porritoxin possesses revised structure 3, not the originally assigned 1. A key reaction was the use of iron pentacarbonyl to formylate an aryllithium when DMF and methyl formate proved insufficiently reactive.
Cornella
Ivan
I
Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Kelly
T Ross
TR
D001685:Biological Factors / Q000138:chemical synthesis*; D004126:Dimethylformamide / Q000737:chemistry; D005561:Formates / Q000737:chemistry; D005563:Formic Acid Esters / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D054354:Iron Carbonyl Compounds; D054833:Isoindoles; D008094:Lithium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry
D001685:Biological Factors; D005561:Formates; D005563:Formic Acid Esters; D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; C466610:porritoxin; C030544:formic acid; D054354:Iron Carbonyl Compounds; C025468:methyl formate; D004126:Dimethylformamide; D008094:Lithium