Prins cyclizations in silyl additives with suppression of epimerization: versatile tool in the synthesis of the tetrahydropyran backbone of natural products.
[reactions: see text] A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis-4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerization in Prins cyclization has also been addressed in the total synthesis of (-)-centrolobine using this methodology.
Chan
Kok-Ping
KP
Divison of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore 637616.
Loh
Teck-Peng
TP
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007536:Isomerism; D008745:Methylation; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*
D001688:Biological Products; D009930:Organic Chemicals; D011714:Pyrans; C432457:centrolobin