Efficient synthesis of (+)-MK7607 and its C-1 epimer via the stereoselective transposition of a tertiary allylic alcohol.
These studies provide an efficient and stereoselective synthetic route to (+)-MK7607 and its C-1 epimer from a common intermediate in high overall yields. The synthetic methodologies mainly rely on the stereospecific 1,3-allylic transposition of the hindered tertiary alcohol group through a palladium-catalyzed allylic rearrangement as well as a PBr(3)-mediated allylic-transposed bromination.
Lim
Chaemin
C
College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Baek
Dong Jae
DJ
Kim
Deukjoon
D
Youn
So Won
SW
Kim
Sanghee
S
D002384:Catalysis; D005690:Galactose / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
C544043:MK7607; D010636:Phenols; D020005:Propanols; C006463:allyl alcohol; D010165:Palladium; D005690:Galactose