Total synthesis of the nonadjacently linked bis-tetrahydrofuran acetogenin bullatanocin (squamostatin C).
The total synthesis of the nonadjacently linked bis-THF acetogenin bullatanocin (squamostatin C) is described. The synthetic strategy is a modular one based on three components, two mono-THF alkenes and a butenolide precursor, and the olefin cross-metathesis and Wittig olefination as the segment-coupling reactions. The synthesis confirms the structure of the natural product, and its convergent design makes it especially attractive for analogue synthesis.
Zhu
Lei
L
Department of Chemistry, Hunter College/CUNY, 695 Park Avenue, New York, New York 10021, USA.
Mootoo
David R
DR
D054378:Acetogenins; D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D037621:Artemisinins / Q000138:chemical synthesis*; D005233:Fatty Alcohols / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D054378:Acetogenins; D000475:Alkenes; D000588:Amines; D000970:Antineoplastic Agents; D037621:Artemisinins; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; C487673:O-aminodihydroartemisinin; C487672:squamostatin C