Synthesis and circular dichroism of steroids with 2,3-dihydro-1-benzofuran and 4H-benzopyran chromophores; revision of the absolute configuration of some norneolignans from Krameria cystisoides

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Abstract

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.

Original languageEnglish
Pages (from-to)453-461
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number3
DOIs
Publication statusPublished - Jan 1 2000

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ASJC Scopus subject areas

  • Chemistry(all)

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