A new short synthesis of 10R-tuberculostearic acid and its enantiomer

Roberts, Ieuan; Baird, Mark S.

doi:10.1016/j.chemphyslip.2006.03.006

Cited by 10 publications

(10 citation statements)

References 32 publications

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“…Several synthetic routes have been described for ( R )-TBSA, but all routes provide the racemate (17)(18)(19)(20)(21)(22)(23)(24) or are based on chiral pool strategies ( 15,25,26 ), so we designed a new catalytic, enantioselective route. Unsaturated thioester 4 ( Fig.…”

Section: Synthesis Of Tbsamentioning

confidence: 99%

Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

Horst

Seshadri

Sweet

et al. 2010

Journal of Lipid Research

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Section: Synthesis Of Tbsamentioning

confidence: 99%

Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

Horst

Seshadri

Sweet

et al. 2010

Journal of Lipid Research

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“…50) and several methods for its synthesis have been reported2526515253. Nevertheless, an updated, shorter and more effective method for accessing this important fatty acid is still desirable.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity

et al. 2015

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Tuberculosis, aggravated by drug-resistant strains and HIV co-infection of the causative agent Mycobacterium tuberculosis, is a global problem that affects millions of people. With essential immunoregulatory roles, phosphatidylinositol mannosides are among the cell-envelope components critical to the pathogenesis and survival of M. tuberculosis inside its host. Here we report the first synthesis of the highly complex tetraacylated phosphatidylinositol hexamannoside (Ac2PIM6), having stearic and tuberculostearic acids as lipid components. Our effort makes use of stereoelectronic and steric effects to control the regioselective and stereoselective outcomes and minimize the synthetic steps, particularly in the key desymmetrization and functionalization of myo-inositol. A short synthesis of tuberculostearic acid in six steps from the Roche ester is also described. Mice exposed to the synthesized Ac2PIM6 exhibit increased production of interleukin-4 and interferon-γ, and the corresponding adjuvant effect is shown by the induction of ovalbumin- and tetanus toxoid-specific antibodies.

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“…The most efficient synthesis reported to date is that of Roberts and Baird who prepared TBSA in four steps from (S)-citronellyl bromide, in a route involving stepwise elongations using copper(I)-catalyzed cross-coupling and Wittig extension. 22 We were inspired by this use of citronellyl bromide as a linchpin, and anticipated that diverting the cross-coupled intermediate into a Grubbs-cross-metathesis/hydrogenation process could provide further synthetic abbreviation. Thus, according to the reported method, 22 copper(I)-catalyzed cross-coupling of hexyl magnesium bromide with (S)-citronellyl bromide afforded the alkene 3 (Scheme 1).…”

Section: Synthesis Of (R)-tuberculostearic Acidmentioning

confidence: 99%

“…22 We were inspired by this use of citronellyl bromide as a linchpin, and anticipated that diverting the cross-coupled intermediate into a Grubbs-cross-metathesis/hydrogenation process could provide further synthetic abbreviation. Thus, according to the reported method, 22 copper(I)-catalyzed cross-coupling of hexyl magnesium bromide with (S)-citronellyl bromide afforded the alkene 3 (Scheme 1). Initially, a 1 : 1 mixture of ethyl 6-heptenoate and 3 were reacted in the presence of Hoveyda-Grubbs II catalyst, affording a 58% yield of an E/Z mixture of crosscoupled alkenes.…”

Section: Synthesis Of (R)-tuberculostearic Acidmentioning

confidence: 99%

Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

2017

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We report the total synthesis of (R)-tuberculostearic acid-containing Mycobacterium tuberculosis phosphatidylglycerol (PG). The approach features a two-step synthesis of (R)-tuberculostearic acid, involving an (S)-citronellyl bromide linchpin, and the phosphoramidite-assisted assembly of the full PG structure. Collision-induced dissociation mass spectrometry of two chemically-synthesized PG acyl regioisomers revealed diagnostic product ions formed by preferential loss of carboxylate at the secondary (sn-2) position.

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A new short synthesis of 10R-tuberculostearic acid and its enantiomer

Cited by 10 publications

References 32 publications

Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity

Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

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