Pinoresinol dimethyl ether

TLC has been finding increasing application in the sphere of wood research. Using chloroform-ethyl acetate (90 + 10) on silica gel G layers, Freijdenberg and Sidhu [54] have separated (+)-sesamin, xRf 78 (-f)-asarinin, 87 (+)-epiasarinin, 93 from (+)-pinoresinol dimethyl ether, 47 and (+)-epipinoresinol dimethyl ether, 55. After spraying with formalin-sulphuric acid (1 + 9) and heating to 110° C, the... 

Cp2TiCl-mediated 5-exo-trig cyclizations have been intensively exploited by Roy et al. for the total synthesis of ( )-dihydroprotolichesterinic and ( )-roccellaric acids, ( )-sesamin, ( )-dihydrosesamin, ( )-acuminatin, ( )-eudesmin, ( )-lariciresinol, ( )-pinoresinol, ( )-piperitol, ( )-acumi-natin methyl ether, (zh)-sanshodiol methyl ether, ( )-piperitol methyl ether, ( )-pinoresinol monomethyl ether, ( )-lariciresinol monomethyl ether, and ( )-lariciresinol dimethyl ether [ 100-103]. Moreover, this group has very recently reported the enantioselective synthesis of (-)-sesamin (Scheme 19), (-)-dihydrosesamin, (-)-acuminatin, and (-)-methyl piperitol by radical cyclization of chiral epoxides initiated by Cp2TiCl [104]. 

The preparation of 21 (Chart 3) by selenium dehydrogenation of the dimethyl ethers of pinoresinol (22) and epipinoresinol (23) was reported (22) prior to the isolation of the furoguaiacins (1.9a, b) from a natural... 

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