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
Publication statusPublished - 2000

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Furans
Benzopyrans
Chromophores
Conformations
Steroids
Cholesterol
Derivatives
1-benzofuran

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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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.",
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T1 - 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

AU - Kurtán, T.

AU - Gács-Baitz, E.

AU - Majer, Zs.

AU - Antus, S.

PY - 2000

Y1 - 2000

N2 - 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.

AB - 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.

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