1993
DOI: 10.1021/np50097a013
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Structural Revisions of Some Non-Adjacent Bis-Tetrahydrofuran Annonaceous Acetogenins

Abstract: The relative stereochemistries of bullatalicin [1] and bullatalicinone [2] were partially reassigned based on COSY and relayed COSY spectra. The structures of annonins VIII [3], IV [4], and XVI [5] were revised and concluded as bullatalicin [1], bullatanocin [6], and squamostatin A [7], respectively.

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Cited by 13 publications
(12 citation statements)
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“…Bullatalicinone: obtained as white powder; mp 125−126 °C; [α] 25 D +23.4° ( c 0.4, CHCl 3 ); UV (MeOH) λ max (log ε) 201 (3.84) nm; MS and 1 H and 13 C NMR data were identical with published values …”
Section: Methodssupporting
confidence: 61%
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“…Bullatalicinone: obtained as white powder; mp 125−126 °C; [α] 25 D +23.4° ( c 0.4, CHCl 3 ); UV (MeOH) λ max (log ε) 201 (3.84) nm; MS and 1 H and 13 C NMR data were identical with published values …”
Section: Methodssupporting
confidence: 61%
“…The locations of these hydroxyls, as well as the planar structures of the molecules, were established by close examination of the EIMS fragmentation (Scheme ). Compared with all the spectral data and the EIMS fragmentation of bullatalicinone, the mixture of 1 and 2 was concluded to be closely related. Thus, the structures of 1 and 2 were determined as shown and named as 20,23- cis -2,4- trans -bullatalicinone ( 1 ) and 20,23- cis -2,4- cis -bullatalicinone ( 2 ).…”
Section: Resultsmentioning
confidence: 92%
See 1 more Smart Citation
“…[a]D = + 13S (c = 0.14, CHCI 3 ) (13,14) IR (13,15,16); UV (13,15) lH nmr (10), (500 MHz) (13,15), (400 MHz) (16); 13C nmr (10), (125 MHz) (13,14,15), (100 MHz) (16) F ABms (13,15,16), F ABms/ms (15), elms (10,15,16), Elms (10,11) HRms (13), HRElms (13,14) tetraacetate: 1 H nmr (10), (500 MHz) (13,14,15) tetra-TMSi derivative: Elms (11) mesitoate: 1 H nmr (C6D6' 500 MHz) (13,14) tetra-( + )-MTPA ester: 1 H nmr (10), (500 MHz) (15) (25) UV (25) lH nmr (500 MHz) (25); 13C nmr (125 MHz) (25) F ABms (25), HRF ABms (25) hexaacetate: 1 H nmr (500 MHz) (25), 13C nmr (125 MHz) (25) TMSi derivative: Elms (25), HRElms (25) …”
Section: Name Of Compoundmentioning
confidence: 99%
“…To date, only two different relative configurations for such acetogenins with non-adjacent THF rings have been encountered: -transthreo/threo-trans-threo and trans-threo/threo-trans-erythro (11,12).…”
Section: Fujimoto Et Al Models (20)mentioning
confidence: 99%