Asymmetric synthesis of spiroketal, spiroether, and oxabicycle building blocks via stereoselective spiro- and bicycloannulation of 2-hydroxy dihydropyrans.
A modular asymmetric synthesis of spiroketal, spiroether, and oxabicycle building blocks is described based on the spiro- and bicycloannulation of alpha-hydroxy dihydropyrans, which were obtained from sulfoximine-substituted homoallylic alcohols. Key steps of the syntheses are stereoselective Ferrier-type O- and C-glycosidation, ring-closing metathesis, and stereoselective Prins cyclization.
Lejkowski
Michal
M
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.
Banerjee
Prabal
P
Runsink
Jan
J
Gais
Hans-Joachim
HJ
D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006859:Hydrogen / Q000737:chemistry*; D006900:Hydroxylation; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
D000475:Alkenes; D004988:Ethers, Cyclic; D005663:Furans; D007097:Imines; D011714:Pyrans; D013141:Spiro Compounds; D013457:Sulfur Compounds; C531272:spiroether; C520774:spiroketal; D006859:Hydrogen; D010100:Oxygen