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Bourgeanic acid

A number of cyclization and condensation reactions have been used to effect 1,5-dioxocin ring closure. Bourgeanic acid, an aliphatic depside isolated from a lichen (Ramalina sp.), cyclizes upon treatment with cold benzenesulfonyl chloride, affording lactone (113) in quantitative yield (Equation (36)) <90JOC5938>. [Pg.629]

Bruun T (1973) Bourgeanic acid in the lichen Stereocaulon tomentosum. Acta Chem Scand 27 3120 Bruun T (1976a) Brassicasterol in Cladonia gonecha and Stereocaulon tomentosum. Phytochemistry 15 1179-1180... [Pg.450]

Bourgeanic acid (78) isolated from Ramalina bourgeana, R. evernioides ( = Niebla evernioides) (18) and Sterepcaulon tomentosum (32) can be considered an aliphatic depside and appears to be a biogenetic oddity since by inspection the component hydroxy acids would appear to arise from three propionate and one acetate units. However labelling experiments... [Pg.120]

Scheme 10. Schematic biosynthetic route to bourgeanic acid... Scheme 10. Schematic biosynthetic route to bourgeanic acid...
Bourgeanic Acid in the Lichen Stereocaulon tomentosum. Acta Chem. Scand. 27, 3120 (1973). [Pg.220]

An enantiospecific synthesis (see Scheme 26) of (-i-)-bourgeanic acid (18) (37) via (-)-hemibourgeanic defines the latter as 2S,3S,4R,6R-3-hydroxy-2,4,6-trimethyloctanoic acid (722, 723). Conformational... [Pg.30]

Whalley WB (1949) The Application of the Modified Gattermann Reaction to Methyl and Ethyl Orsellinate. J Chem Soc 3278 72/. White FJ, James PW (1985) A New Guide to Microchemical Techniques for the Identification of Lichen Substances. British Lichen Soc Bull 57 1 722. White JD, Johnson AT (1990) Synthesis of the Lichen Metabolite (+)-Bourgeanic Acid and Conformational Analysis of its Dilactone. J Org Chem 55 5938 725. White JD, Johnson AT (1994) Synthesis of the Aliphatic Depside (+)-Bourgeanic acid. J Org Chem 59 3347... [Pg.274]

Yadav JS, Rao KVR, Ravindar K, Subba Reddy BV. Total synthesis of (+)-bourgeanic acid utilizing desymmetrization strategy. Eur. J. Org. Chem. 2011 58-61 and references therein. [Pg.317]

See other pages where Bourgeanic acid is mentioned: [Pg.593]    [Pg.626]    [Pg.628]    [Pg.631]    [Pg.35]    [Pg.37]    [Pg.51]    [Pg.98]    [Pg.99]    [Pg.114]    [Pg.143]    [Pg.143]    [Pg.472]    [Pg.121]    [Pg.122]    [Pg.122]    [Pg.123]    [Pg.31]    [Pg.31]   
See also in sourсe #XX -- [ Pg.143 ]

See also in sourсe #XX -- [ Pg.120 , Pg.121 , Pg.122 , Pg.123 ]

See also in sourсe #XX -- [ Pg.31 ]



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