Gold-catalyzed transannular [4+3] cycloaddition reactions.
Macrocyclic propargyl acetates containing a furan ring were prepared by using a CrCl(2)-promoted reaction. In the presence of either a Au(I) or Au(III) catalyst, a tandem 3,3-rearrangement/transannular [4+3] cycloaddition reaction occurred to give propargyl acetates that are regio- and diastereospecific. The regiochemistry of the product is controlled by the position of the acetoxy group in the starting material and the stereochemistry of the reaction depends on the ring size.
Gung
Benjamin W
BW
Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, USA. gungbw@muohio.edu
Craft
Derek T
DT
Bailey
Lauren N
LN
Kirschbaum
Kristin
K
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D050607:Organogold Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D005663:Furans; D050607:Organogold Compounds; D011083:Polycyclic Compounds; C531521:cortistatin A; D006046:Gold