Synthesis and Characterization ofall-E-(4,4′-13C2)-Astaxanthin Strategies for Labelling the C15-End Groups of Carotenoids

Jansen, F. J. H. M.; Lugtenburg, J.

doi:10.1002/(sici)1099-0690(200003)2000:5<829::aid-ejoc829>3.0.co;2-z

Cited by 11 publications

(15 citation statements)

References 18 publications

(17 reference statements)

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“…This phothocycloaddition gave a single 1:1 adduct 136 after a retroaldol opening of the unstable hydroxycyclobutane formed [39]. Cyclofarnesine R (28) and 3-hydroxycyclofarnesine R (152) were prepared from allyl bromide 143 (Scheme 19) [40] in eleven or twelve steps, respectively. Cyclofarnesine R ( 28 Preparation of -apo-12-carotenol (171) [4] was carried out from βionone in three steps (HWE olefination, reduction and reduction again) (Scheme 22).…”

Section: Synthesis Of Other C18 Apocarotenoidsmentioning

confidence: 99%

Occurrence and Chemical Synthesis of Apocarotenoids from Mucorales: A Review

Barrero

Pino

Arteaga

et al. 2017

Natural Product Communications

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Apocarotenoids are metabolites originated by degradation of carotenes through the loss of carbon atoms placed at the side chain of their structure as consequence of oxydative reactions. We present here the first review of apocarotenoids in the fungi mucorales Phycomyces blakesleeanus, Blakeslea trispora and Mucor mucedo. This review is divided into two parts: the first one presents their structures and sources, whereas the second part is dedicated to their chemical synthesis.

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Section: Synthesis Of Other C18 Apocarotenoidsmentioning

confidence: 99%

Occurrence and Chemical Synthesis of Apocarotenoids from Mucorales: A Review

Barrero

Pino

Arteaga

et al. 2017

Natural Product Communications

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“…Several routes to trisporoids such as trisporins, methyl trisporates, trisporols, and free trisporic acids have been developed and reported [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34]. The disadvantage of most routes is the large number of steps required for the synthesis of the final targets and the lack of flexibility to produce early and late trisporoids along the same protocol using common intermediates.…”

Section: Open Accessmentioning

confidence: 99%

Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

et al. 2014

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Abstract:The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C-3, C-8 and C-9, and a  1,6 -double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms.

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“…Treatment of product 41 with a base gives (4RS)-4hydroxy-β-cyclocitronitrile 42 (Lugtenburg et al, 1999;Jansen, 2000). Pyridinium chlorochromate oxidation and subsequent ketalisation with ethylene glycol gives compound 43 which upon DIBAL-H reduction gives the 4,4΄-protected β-cyclocitral 44.…”

Section: Scheme 8 Preparation Of the End Group Of Canthaxanthin In Amentioning

confidence: 99%

Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions.

Lugtenburg¹,

Dawadi²

2012

Acta Biochim Pol

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Carotenoids and their metabolites are essential factors for the maintenance of important life processes such as photosynthesis. Animals cannot synthesize carotenoids de novo, they must obtain them via their food. In order to make intensive animal husbandry possible and maintain human and animal health synthetic nature identical carotenoids are presently commercially available at the multi-tonnes scale per year. Synthetically accessible (13)C enriched carotenoids are essential to apply isotope sensitive techniques to obtain information at the atomic level without perturbation about the role of carotenoids in photosynthesis, nutrition, vision, animal development, etc. Simple highly (13)C enriched C(1), C(2) and C(3) building blocks are commercially available via 99% (13)CO. The synthetic routes for the preparation of the (13)C enriched building blocks starting from the commercially available systems are discussed first. Then, how these building blocks are used for the synthesis of the various (13)C enriched carotenoids and apocarotenoids are reviewed next. The synthetic Schemes that resulted in (13)C enriched β-carotene, spheroidene, β-cryptoxanthin, canthaxanthin, astaxanthin, (3R,3'R)-zeaxanthin and (3R,3'R,6'R)-lutein are described. The Schemes that are reviewed can also be used to synthetically access any carotenoid and apocarotenoid in any (13)C isotopically enriched form up to the unitarily enriched form.

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Synthesis and Characterization ofall-E-(4,4′-13C2)-Astaxanthin Strategies for Labelling the C15-End Groups of Carotenoids

Cited by 11 publications

References 18 publications

Occurrence and Chemical Synthesis of Apocarotenoids from Mucorales: A Review

Occurrence and Chemical Synthesis of Apocarotenoids from Mucorales: A Review

Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions.

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