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Hardwickiic acid

The widespread occurrence of the clerodane skeleton is exemplified by the isolation of (—)-hardwickiic acid (25), the C-15 monomethyl ester of kolavenic acid, and two furanoid substances, agbaninol (26, R = H) and agbanindiol B (26, R = OH) from Gossweilerodendron balsamiferum (Caesalpiniaceae). Agbanindiol A has the structure (27). These compounds have been correlated with kolavenic acid and hardwickiic acid. [Pg.129]

Gambarro et al. [29] reported the isolation and characterization of four clerodane derivatives, two of them new hardwickiic acid, Fig. (7) and hautriwaic acid, Fig. (8) present in Baccharis macraei Hook et Am, a shrub that grows in the coastal area of Central Chile, while Baccharis paniculata D. C. from Northern Chile also yielded two new weo-clerodane diterpenoids [30],... [Pg.710]

A new diterpenoid (18), related to hardwickiic acid, has been isolatedfrom Annona coriacea. The furan (19) was also isolated from this source. A further... [Pg.166]

Juvabione, T2.16 Epijuvabione, T2.1 Hardwickiic acid deriv., T"36.4 Juvenile hormone III, T"11.8... [Pg.235]

Hardwickiic acid, H-70002 Hebemacrophyllide, H-60010 en/-3/ -Hydroxy-15-beyerene-2,12-dione, in D-80285... [Pg.669]

Hardwickiic acid (ent 404) has been isolated from the heartwood of Copaifera officinalis (104). Agbanindiol-B (405) and related compounds from wood of Gassweilerodendron balsamiferum provide other examples of trans-... [Pg.752]

Cocker W, Moore A L, Pratt A C 1965 Dextrorotatory hardwickiic acid, an extractive of Copaifera officinalis. Tetrahedron Lett 1983-1985... [Pg.795]

Misra R, Pandey R C, Sukh Dev 1979 Higher terpenoids. VIII. Diterpenoids from the oleoresin of Hardwickia pinnata. Part I hardwickiic acid. Tetrahedron 35 2301-2310... [Pg.802]

Solidago-18-oic acid, 8-epi- [Reported as 53 10a-trans-clerodane probably (-)-hardwickiic acid]... [Pg.39]

Structural correlation of solidagonic acid with 495 and 475 was made feasible by the recent assignment by Misra and coworkers 391) of absolute stereochemistry to the chiral centers of the Hardwickia pinnata clerodanes, (-)-hardwickiic acid (511), kolavenic acid, and kolavenol (Figure 34 [p. 515]). Their pivotal work on clerodane stereochemistry proceeded as described below ... [Pg.493]

Co-occurrence with (-)-hardwickiic acid of known absolute stereochemistry (391) also led to the assignment of its stereochemistry to the clerodane constituents of S. juncea (318). [Pg.494]

The Centipeda compound 249 assignment was based on correlation with the Solidago (286) trans-ent-dcrodane, (-)-hardwickiic acid. The discrepancy between the structure illustrated for 249 and that of (-)-hardwickiic acid was not discussed. Possibly, the above-described confusion results from incorrectly illustrated structures for 248, 249, and 251. Because 249 was described as being previously reported by Misra et al. (391), it is assumed that this structure is actually (-)-hardwickiic acid and is probably identical to 245. The other structures, 248 and 250, are presumably the same compound and identical to 1,2-dehydro-(-)-hardwickiic acid. Very likely, 248 and 249 are the same as 250 and 245, respectively. [Pg.496]

Figure 34. Chemical degradation of (-)-hardwickiic acid (511) to products permitting the assignment of ring-fusion configuration (391). Figure 34. Chemical degradation of (-)-hardwickiic acid (511) to products permitting the assignment of ring-fusion configuration (391).
Figure 36. Attempts to correlate the structure of solidagoic acid A (239) with those of known cis-clerodanes A. comparison of the methyl H-NMR chemical shifts (6) of a solidagoic acid A derivative, 239a, to those of a (-)-hardwickiic acid derivative, 507 B. enone derivative (239b) of solidagoic acid A and the revised structure of plathyterpenone used for comparison of CD optical properties. Figure 36. Attempts to correlate the structure of solidagoic acid A (239) with those of known cis-clerodanes A. comparison of the methyl H-NMR chemical shifts (6) of a solidagoic acid A derivative, 239a, to those of a (-)-hardwickiic acid derivative, 507 B. enone derivative (239b) of solidagoic acid A and the revised structure of plathyterpenone used for comparison of CD optical properties.
Misra, R., R.C. Pandey, and Sukh Dev The absolute stereochemistry of hardwickiic acid and its congeners. Tetrahedron Letters 1968, 2681. [Pg.571]

Rustaiyan, A., E. Simozar, A. Ahmadi, M. Grenz, and F. Bohlmann A hardwickiic acid derivative from Pulicaria gnaphalodes, Phytochem. 20, 2772 (1981). [Pg.573]

Hardwickiic acid, T37 Hastanecine, K22 Havanensin, T53 Hecogenin, T49 Hedycarol, T20 Helenalin, T24 Helicenes, X7, X6 ... [Pg.162]

See other pages where Hardwickiic acid is mentioned: [Pg.802]    [Pg.108]    [Pg.710]    [Pg.167]    [Pg.95]    [Pg.247]    [Pg.668]    [Pg.114]    [Pg.275]    [Pg.305]    [Pg.752]    [Pg.41]    [Pg.41]    [Pg.42]    [Pg.43]    [Pg.494]    [Pg.494]    [Pg.494]    [Pg.496]    [Pg.498]    [Pg.602]    [Pg.602]    [Pg.602]    [Pg.602]   
See also in sourсe #XX -- [ Pg.30 , Pg.710 , Pg.711 ]

See also in sourсe #XX -- [ Pg.710 , Pg.711 ]

See also in sourсe #XX -- [ Pg.36 , Pg.37 ]

See also in sourсe #XX -- [ Pg.752 ]



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