Starting from cholesterol the 2,3-dihydrobenzo[b]furans 12a, 12b, and the 4H-benzopyran derivative 14 with known absolute conformation were synthesized by a stereocontrolled sequence. The same helicity rule was found to be valid for both chromophores; the P/M helicity of the heteroring leads to a negative/positive CD within the α-band. On the basis of this rule the absolute configuration of norneolignans 24-26 isolated from Krameria cystisoides was also revised.
|Number of pages||9|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - Jan 1 2000|
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