Synthesis of (±)-amathaspiramide F and discovery of an unusual stereocontrolling element for the [2,3]-Stevens rearrangement.
A formal total synthesis of (±)-amathaspiramide F through a tandem palladium-catalyzed allylic amination/[2,3]-Stevens rearrangement is reported. The unexpected diastereoselectivity of the [2,3]-Stevens rearrangement was controlled by the substitution patterns of an aromatic ring. This discovery represents a new stereocontrolling element for [2,3]-sigmatropic rearrangements in complex molecular settings.
Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas , 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.
Arash
A
Soheili
Uttam K
UK
Tambar
D000498:Allyl Compounds / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000498:Allyl Compounds; D011759:Pyrrolidines; D013141:Spiro Compounds; C471225:amathaspiramide F; D010165:Palladium