The dihydrofuran template approach to furofuran synthesis

Aldous, David; Batsanov, Andrei S.; Yufit, D. S.; Dalencon, Anne J.; Dutton, William M.; Steel, Patrick G.

doi:10.1039/b604952d

Cited by 27 publications

(9 citation statements)

References 37 publications

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“…δ C (100 MHz; CDCl 3 ) 14.5 (1-OCH 2 C H 3 ), 60.5 (1-OCH 2 CH 3 ), 101.7 (-OCH 2 O-), 106.6 (C-5′), 108.7 (C-2′), 116.4 (C-2), 124.5 (C-6′), 129.1 (C-1′), 144.4 (C-3), 148.5 (C-4′), 149.7 (C-3′), 167.3 (C-1). Values are in agreement with literature data [44].…”

Section: Methodssupporting

confidence: 92%

Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans

et al. 2018

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Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.

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Section: Methodssupporting

confidence: 92%

Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans

et al. 2018

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“…The (À)-enantiomer of asarinin seems to be the prevalent form in nature (as judged from citations in Chemical Abstracts, but we have not counted these exactly). The naturally occurring stereoisomers epiasarinin (inverted at C6) and sesamin (inverted at C5) are also known; for a brief overview, see Aldous et al (2006). A search of the Cambridge Structural Database (CSD, Version 5.33; Allen, 2002; see also Table 1) reveals that several crystal structures have been reported, but in some cases confusion may have arisen.…”

Section: Commentmentioning

confidence: 99%

“…A search of the Cambridge Structural Database (CSD, Version 5.33; Allen, 2002; see also Table 1) reveals that several crystal structures have been reported, but in some cases confusion may have arisen. For epiasarinin, the structure of the synthetic racemate was determined by Aldous et al (2006; we adopt an analogous atom-numering scheme for the racemate of asarinin), but no enantiomerically pure structure has yet been determined. Three closely similar structures of sesamin have been reported, by Baures et al (1992), Hsieh et al (2005) and Li et al (2005).…”

Section: Commentmentioning

confidence: 99%

(±)-Asarinin

Negi¹,

Negi²,

Kumar³

et al. 2012

Acta Crystallogr C

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Asarinin, C(20)H(18)O(6), was isolated as a racemate from the shrub Zanthoxylum alatum. Both forms of the enantiomerically pure substance, (+)- and (-)-asarinin, have been the subject of a total of five previous structure determinations that are essentially identical except for the absolute stereochemistry. However, there seems to be some confusion in the literature concerning these structure determinations of asarinin and also those of its stereoisomer sesamin. The molecular structure of racemic asarinin differs from that of the pure enantiomers in the orientation of one ring system. In the packing of the racemate, molecules are linked by C-H...O interactions to form ribbons parallel to [101].

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“…Reagents and conditions: (a) Ph3P + CH2OCH2CH=CH2, t-BuOK, PhCH3, 0 °C; (b) C6H6, 80 °C; (c) NaBH4, MeOH, 0 °C.Njardarson reported85 an asymmetric variant of methodology for 2-arylpyrroline synthesis originally described by Steel 86. In one application, addition of the dienolate derived from ethyl bromocrotonate to chiral sulfinylimine 107 (Scheme 19) afforded the (2S)-alkylpyrroline 108 as a single diastereomer.…”

mentioning

confidence: 99%