7329-28-4Relevant articles and documents
Synthesis of (+)-1,3:2,5-Dianhydroviburnitol ((+)-(1R,2R,3S,5R,6S)-4,7-Dioxatricyclo3,6>octan-2-ol)
Drian, Claude Le,Vogel, Pierre
, p. 1399 - 1405 (2007/10/02)
Epoxidation of (-)-(1R,2R,4R)-2-endo-cyano-7-oxabicyclohept-5-en-2-exo-yl acetate ((-)-5) followed by saponification afforded (+)-(1R,4R,5R,6R)-5,6-exo-epoxy-7-oxabicycloheptan-2-one ((+)-7).Reduction of (+)-7 with diisobutylaluminium hydride (DIBAH) gave (+)-1,3:2,5-dianhydroviburnitol (= (+)-(1R,2R,3S,4R,6S)-4,7-dioxatricyclo3,6>octan-2-ol; (+)-3).Hydride reductions of (+/-)-7 were less exo-face selective than reductions of bicycloheptan-2-one and its derivatives with NaBH4, AlH3, and LiAlH4 probably because of smaller steric hindrance to endo-face hydride attack when C(5) and C(6) of the bicycloheptan-2-one are part of an exo oxirane ring.
STEREOCHMICAL REQUIREMENTS FOR FRAGMENTATION OF HOMOALLYLIC EPOXY ALCOHOLS
Holton, Robert A.,Kennedy, Robert M.
, p. 4455 - 4458 (2007/10/02)
The fragmentation of 5,6-epoxynorbornan-2-ol and 5,6-epoxynorbornan-2-one have been studied under both acidic and basic conditions.These processes show a clear preference for syn periplanar alignment of breaking bonds.
