Rolliniastatin

Rolliniastatin-1 (tetrahydrofuran acetogenin) Rollinia sylvatica (Annonaceae) ETC - NADH-UQOR complex I (0.3nM InM)... [Pg.566]

Rolliniastatin I reported, and successful X-ray studies on p-bromophenylurethane derivative establish complete relative configuration. [Pg.256]

H NMR correlation method further validated by comparison of rolliniastatin I NMR data with the now known relative configuration. Method made more quantitative, relying less on visual inspection. Relative configuration of bis-THF moiety of asimicin verified. [Pg.256]

Figure 8. Graphical Comparison of Proton Chemical Shift Data for Model bis-Acetates 11a-l and the Peracetate Derivatives of Uvaricin (12), Rolliniastatin I (14), and Asimicin (15).

A comment must be made at this point about the limitations of this method. It leaves open the question of directionality of the stereochemical relationships. For example, were the complete relative configuration of rolliniastatin I (8) not known from the x-ray crystallographic study, it would not be possible to tell whether the order of relative configurational relationships proceeding from C(15) to C(24) was threo/cis/threo/cis/erythro or erythro/cis/threo/cisAhreo. We refer to this as the "endedness" problem, and it is an issue of structural ambiguity that has been overlooked in a number of instances. [Pg.262]

Figure 15. Absolute Configuration of the A2 Subunit in Builatacin (5), Asimicin (13), Rolliniastatin 1 (8), Annonacin (3), and Annonacin-10-one (26) Is (4R,36S) [or (4f ,34S) for 3 and 26] from Comparison of their Mosher Esters with Those of Synthetic Modei Compounds 28.

Rolliniastatin-1 was isolated in 1987 from Rollinia mucosa (62), and since then has been found in several species of Annonaceae (4a-b). Koert reported the total synthesis of ew-rolliniastatin-1 110 from L-glutamic acid. The strategy is a sequential synthesis, using as a key step the diastereoselective copper catalyzed Grignard addition on aldehydes (Fig. 12). [Pg.210]

AA48 4-hydroxy-25-hydroxyneorollinicin (Rolliniastatin 1) adjacent bis-THF 4, 15-24 thltlthltler C37H66O7 622... [Pg.981]

AA48 4-hydroxy-25- hydroxyneorolli nicin (Rolliniastatin 1) unripe fruit ... [Pg.985]

Annonin I (Squamocin) Asimicin Rolliniastatin 1 Rolliniastatin 2 Bullatacin l-srHeell C37H66O7 622.93 622.93 wax 81 -83 wax 73-76 cryst. 69-70 Annona squamosa, Uvaria narum Annona squamosa, Asimina triloba, Rollinia mucosa 120298-30-8 102989-24-2 111056-97-4 121917-13-3 123123-32-0... [Pg.38]

Aldehydes and alcohols can be generated by the Pummerer rearrangement and many examples exist. For example, Lee et al. employed this reaction in their synthesis of the natural product rolliniastatin 1, among others. The reaction requires the addition of base and proceeds in good yield. [Pg.343]

See also in sourсe #XX -- [ Pg.150 ]

See also in sourсe #XX -- [ Pg.2 , Pg.6 , Pg.13 ]

See also in sourсe #XX -- [ Pg.262 , Pg.272 ]

See also in sourсe #XX -- [ Pg.2 , Pg.17 , Pg.18 , Pg.26 , Pg.208 , Pg.262 , Pg.272 , Pg.793 ]

See also in sourсe #XX -- [ Pg.2 , Pg.208 , Pg.209 ]

See also in sourсe #XX -- [ Pg.2 , Pg.17 , Pg.262 , Pg.272 ]

See also in sourсe #XX -- [ Pg.793 ]

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