90734-36-4Relevant articles and documents
Wagner-Meerwein Rearrangements in Taraxasterol and Pseudotaraxasterol
Anjaneyulu, A. S. R.,Anjaneyulu, V.,Prasad, K. Harishandra,Rao, G. Sambasiva,Suryanarayana, P.
, p. 1179 - 1183 (2007/10/02)
Both taraxasterol (I) and pseudotaraxasterol (II) give A-nor-3,4-dichloro products (IV) and (VI) respectivly when heated with PCl5 in n-hexane.With POCl3 in pyridine I and II give the same product (VII) without contraction of ring-A while solvolysis of their respective tosylates (X and XII) gives a different, but identical product (XI) from both, attended by contraction of ring-A.Both the tosylates (X and XII) are found to undergo, detosylation when passed through a column of silica gel giving VII and V respectively.The Wagner-Meerwein rearrangements noticed in thesetwo compounds have been rationalised mechanistically.