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Protolichesterinic acid

R = n-Ci2H24C02H (+)-Protopraesorediosic acid (9) R = n-Ci3H27 (+)-Protolichesterinic acid (10)... [Pg.45]

The same strategy was also employed in the synthesis of the saturated analogue of protolichesterinic acid ( )-dihydroprotolichesterinic acid (4) can be synthesized using epoxide 32 as a starting material for the intramolecular radical cyclization to yield 33 as the major diastereomer (Scheme 5). Subsequent oxidation gave finally rise to ( )-4, which could be obtained in di-astereomerically pure form by fractional crystallization. [Pg.48]

Functionalized y-acyloxy-a,yS-unsaturated esters provided yet another versatile strategy towards paraconic acids as exemplified with the synthesis of protolichesterinic acid ((-i-)-lO) (Scheme 22) [60]. The prerequisite precur-... [Pg.63]

Another possibility is the addition of malonate anions to epoxides (equation 75), which, via the alkox-ide ester (199), deliver the lactone ester (200) immediately. This concept has been used in the non-stereocontrolled synthesis of protolichesterinic acid ester (203) from (201) via (202 equation 76). ... [Pg.354]

Another traditional medicine from Iceland, a lichen (Cetaria islandica), is used to treat gastrointestinal ailments and has also been shown to have anti-HP activity [88]. Protolichesterinic acid. Fig. 8, an aliphatic a-methylene-y-lactone, was... [Pg.435]

Loeffler, A., Pratt, R. D., Pucknat, J., Gelbart, G., Dreiding, A. S. Preparation of a-methylenebutyrolactones by the Reformatskii reaction synthesis of protolichesterinic acid. Chimia 1969, 23, 413-416. [Pg.661]

Conjugate addition-acylation. Damon and Schlessinger have reported a stereospecific synthesis of ( )-protolichesterinic acid (5) from the butenolide (1). ... [Pg.210]

Protolichesterinic acid MuroUc acid Lichesterinic acid Neuropogonic acid... [Pg.18]

B Protolichesterinic acid exceedingly thin square-like rhombic plates which form... [Pg.48]

CD (in MeOH) AE257 + 0.32, Ae22o - 9.62 Deriv Addition product of CHjNj to (-)-protohchesterinic acid prisms (MeOH) of mp 61 °C, [a] - 288 (CHCI3), by treatment of (-)-protolichesterinic acid with excessive CH2N2 at room temperature for 4h StL Cetraria ericetorum Opiz [(-)-protoliches-terinic acid)], Cetraria islandica (L.) Ach. [(+)-protolichesterinic acid]... [Pg.152]

Damon RE, Schlessinger RH (1976) An efficient and stereospecific total synthesis of dl-protolichesterinic acid. Tetrahedron Lett 1561-1564... [Pg.453]

Murta MM, Azevedo MBM de, Greene AE (1993) Synthesis and absolute stereochemistry of (-)-protolichesterinic acid, antitumor antibiotic lactone from Cetraria islandica. J Org Chem 58 7537-7541... [Pg.466]

See other pages where Protolichesterinic acid is mentioned: [Pg.222]    [Pg.48]    [Pg.48]    [Pg.59]    [Pg.67]    [Pg.70]    [Pg.364]    [Pg.385]    [Pg.385]    [Pg.46]    [Pg.435]    [Pg.435]    [Pg.435]    [Pg.486]    [Pg.186]    [Pg.381]    [Pg.521]    [Pg.70]    [Pg.309]    [Pg.32]    [Pg.32]    [Pg.37]    [Pg.54]    [Pg.113]    [Pg.113]    [Pg.142]    [Pg.152]    [Pg.465]   
See also in sourсe #XX -- [ Pg.75 ]

See also in sourсe #XX -- [ Pg.48 , Pg.59 , Pg.67 ]

See also in sourсe #XX -- [ Pg.75 ]

See also in sourсe #XX -- [ Pg.3 , Pg.5 , Pg.5 , Pg.9 , Pg.9 , Pg.9 ]

See also in sourсe #XX -- [ Pg.75 ]

See also in sourсe #XX -- [ Pg.366 ]

See also in sourсe #XX -- [ Pg.186 ]

See also in sourсe #XX -- [ Pg.117 , Pg.118 ]

See also in sourсe #XX -- [ Pg.7 , Pg.13 , Pg.33 , Pg.35 , Pg.36 , Pg.228 ]



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