28071-35-4Relevant academic research and scientific papers
Synthesis of the Lignan (+/-)-Dihydrosesamin: Problems of Stereocontrol in the Formation of 2,3,4-Trisubstituted Tetrahydrofurans and Tetrahydrofuranones
Stevens, David R.,Whiting, Donald A.
, p. 425 - 426 (1990)
It is shown that the stereochemistry of addition reactions to 3-arylidene lactones (3) and (9) is controlled by the 5- rather than the 4-substituent: synthesis of the 2,3-trans 3,4-cis lignan dihydrosesamin (11) thus requires use of the 4,5-cis lactone (8), with epimerisation at C-2 following establishment of 3,4-cis geometry.
Stereospecific Synthesis of the 2,3-trans-3,4-cis Trisubstituted Tetrahydrofuran Lignan(+/-)-Dihydrosesamin
Stevens, David R.,Whiting, Donald A.
, p. 633 - 637 (2007/10/02)
It is shown that the stereochemistry of additions to the 3-arylidene lactones 3 and 9 is controlled by the 5- rather than the 4-substituent; synthesis of the 2,3-trans-3,4-cis lignan dihydrosesamin 11b (R = H) thus requires use of the 4,5-cis- lactone 8,
