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Carotenoids: Volume 2: Synthesis by Hanspeter Pfander

"Carotenoids, Volume 2" is the first book to be devoted entirely to the chemical synthesis of carotenoids. The essential in-depth appreciation of the perspectives, principles and strategies of carotenoid synthesis is provided in the first chapter. Preparation of polyene synthons and carotenoid end groups, and the coupling reactions commonly used for carbon-carbon double bond formation, as well as the application of these methods and synthons for the synthesis of carotenoids, are then described in detail. The commercially important technical syntheses used for the large scale industrial production of carotenoids, and methods for the preparation of isotopically labelled carotenoids, in particular for biological and medical applications, are also covered. Following the practice established in Volume 1A, Worked Examples are presented. These describe in detail reliable and efficient procedures for key reactions and can be used to form the basis of practical exercises for students of organic chemistry. Tables of useful synthons and a list of natural carotenoids that have been prepared by total synthesis are included as appendices.

Product Details

ISBN-13: 9783034893251
Publisher: Birkhauser Basel
Publication date: 11/01/2011
Series: Carotenoids Series , #2
Edition description: Softcover reprint of the original 1st ed. 1996
Pages: 362
Product dimensions: 6.69(w) x 9.45(h) x 0.03(d)

Table of Contents

1: General Aspects.- I: Synthesis in Perspective.- II: Strategies for Building the Carbon Skeleton.- A. Introduction.- B. General Strategies.- C. Examples.- 1. Wittig reaction: Astaxanthin and zeaxanthin.- 2. Julia sulphone coupling: Zeaxanthin.- 3. Wittig reaction with unsymmetrical carotenoids: (S)-Trisanhydrobacterioruberin.- 4. Dimerization: ?,?-Carotene.- References.- III: Characterization of Products.- A. Introduction.- B. Isomers of ?,?-carotene.- C. (7Z)-Lycopene.- D. Lutein.- E. Zeaxanthin.- F. 3,4,3?,4?-Tetraacetoxypirardixanthin.- References.- 2: Coupling Reactions.- I: Enol Ether and Aldol Condensations.- A. Introduction.- B. Enol Ether Condensations.- 1. Alkyl enol ethers.- 2. Trimethylsilyl enol ethers.- C. Aldol Condensations.- References.- II: Organometallic Reactions.- A. Introduction.- B. General Procedures.- C. Metals of Groups IA, IIA and IIIB (Li, Na, Mg and Zn).- 1. Metal acetylides (alkynylides).- 2. Metal alkenyls.- 3. Allylic alkali metal derivatives.- 4. Zinc reagents.- D. Palladium-mediated and Nickel-mediated Reactions.- 1. Palladium.- 2. Nickel.- E. Copper.- 1. Cadiot-Chodkiewicz coupling reaction.- 2. Cuprates.- F. Low-valent Titanium.- References.- III: Wittig Olefination.- A. Introduction.- B. Phosphorus Ylides.- 1. Reactivity of phosphorus ylides.- 2. Production of phosphorus ylides.- C. Stereochemistry.- 1. Factors that influence stereoselectivity.- 2. Steric control.- D. Reaction Mechanisms.- E. Horner-Wadsworth-Emmons Olefination.- F. Use of the Wittig Reaction in Carotenoid Synthesis.- 1. Introduction.- 2. Bond formation between C(7)/C(8), or C(7?)/C(8?).- 3. Bond formation between C(11)/C(12), or C(11?)/C(12?).- 4. Bond formation between C(15)/C(15?).- References.- IV: Sulphone Coupling.- A. Alkylation — Elimination Method.- 1. Synthesis of vitamin A derivatives.- 2. Synthesis of carotenoids.- B. Double Elimination Method.- References.- 3: Carotenoid Synthesis.- I: Polyene Synthons.- A. Introduction.- B. Symmetrical Central C10-Components.- 1. C10-Components of various functionality.- 2. Industrial routes to the C10-dialdehyde.- 3. Unsymmetrically functionalized central C10-components.- C. Synthesis of Protected C15- and C20-Dialdehydes.- D. C10-Components for the Synthesis of Segments C(8) to C(15) and C(15?) to C(8?).- E. 1,4-Bifunctional Isoprenoid C5-Building Blocks.- 1. (E)-4-Acetyloxy-2-methylbut-2-enal.- 2. Monoacetals of (E)-2-methylbut-2-ene-1,4-dial.- 3. C5-Phosphonium ester salts and C5-phosphonate esters.- 4. 5-Hydroxy-4-methyl-2(5H)-furanone.- References.- II: Acyclic Carotenoids.- A. Introduction.- B. Carotenoids with the ? End Group.- C. Carotenoids with the 3,4-Didehydro-? End Group.- D. Carotenoids with the 1,2-Dihydro-? End Group.- E. Carotenoids with the l-Hydroxy-3,4-didehydro-l,2-dihydro-? End Group.- F. Carotenoids with the l-Methoxy-3,4-didehydro-l,2-dihydro-? End Group.- G. Carotenoids with the 1-Hydroxy-1,2-dihydro-? End Group.- H. Carotenoids with the 16-Hydroxy-? End Group.- I. Carotenoids with the l,2-Dihydroxy-3,4-didehydro-l,2-dihydro-? End Group.- J. Carotenoids with the 1,2-Epoxy-1,2-dihydro-? End Group.- K. Carotenoids with the 1-Methoxy-2-keto-3,4-didehydro-l,2-dihydro-? End Group.- L. C45- and C50-Carotenoids.- M. Diapocarotenoids.- References.- III: Synthesis of Cyclic Carotenoids.- A. Introduction.- B. Carotenoids with the ? End Group.- 1. ?,?-Carotene.- 2. Carotenoids with the 3,4-didehydro-? end group.- 3. Retro-carotenes.- 4. Carotenoids with the 2-hydroxy-? end group.- 5. Carotenoids with the 3-hydroxy-? end group.- 6. Carotenoids with the 4-hydroxy-? end group.- 7. Carotenoids with the 3,4-dihydroxy-? end group.- 8. Carotenoids with the 5,6-dihydroxy-5,6-dihydro-? end group.- 9. Carotenoids with the 3,5,6-trihydroxy-5,6-dihydro-? end group.- 10. Carotenoids with the 5,6-epoxy-5,6-dihydro-? end group.- 11. Carotenoids with the 5,8-epoxy-5,8-dihydro-? end group.- 12. Carotenoids with the 3-hydroxy-5,6-epoxy-5,6-dihydro-? end group.- 13. Carotenoids with the 2-oxo-3,4-didehydro-? end group.- 14. Carotenoids with the 3-oxo-retro-? end group.- 15. Carotenoids with the 4-oxo-? end group.- 16. Carotenoids with the 3-hydroxy-4-oxo-? end group.- C. Carotenoids with the ? End Group.- 1. ?,?-Carotene and ?,?-carotene.- 2. Carotenoids with the 3-hydroxy-? end group.- D. Carotenoids with the ? End Group.- E. Carotenoids with the ? End Group.- F. Carotenoids with Aromatic End Groups.- 1. Carotenoids with the ? end group.- 2. Carotenoids with the 3-hydroxy-? end group.- 3. Carotenoids with the ? end group.- G. C50-Carotenoids.- 1. Carotenoids with a substituted ? end group.- 2. Carotenoids with a substituted ? end group.- 3. Carotenoids with a substituted ? end group.- H. Norcarotenoids.- References.- IV: Synthesis of Acetylenic, Allenic and In-chain Substituted Carotenoids.- A. Introduction.- B. Synthesis of Acetylenic Carotenoids.- C. Synthesis of Allenic Carotenoids.- D. Synthesis of Butenolide Carotenoids.- 1. Sulphone method.- 2. Synthesis of the optically active C15-epoxyformyl ester.- 3. Synthesis of the optically active C22-allenic sulphone with an abnormal location of the in-chain methyl group.- 4. Synthesis of optically active peridinin.- E. Synthesis of ?-Diketone Carotenoids.- 1. The aldol condensation route.- 2. The Wittig condensation route.- 3. The Claisen condensation route.- References.- V: Total Synthesis of (Z)-Isomers.- A. Introduction.- B. Strategy.- C. Formation of (Z)-Double Bonds by Synthesis.- 1. Sterically unhindered disubstituted (Z)-double bond (15Z).- 2. Sterically hindered disubstituted (Z)-double bonds (7Z and 11Z).- 3. Trisubstituted (Z)-double bonds (5Z, 9Z and 13Z).- 4. Thermodynamicly favoured cis double bonds.- D. Direct synthesis of (Z)-isomers.- 1. Carotenes.- 2. Xanthophylls.- 3. Apocarotenoids.- References.- VI: Labelled Carotenoids.- Synthesis.- 1. Synthesis and use of 13C-labelled synthons.- 2. Synthesis of the central C10-unit with 13C-labels.- 3. Synthesis of unlabelled synthons.- 4. Synthesis of labelled carotenoids.- 5. Deuterium-labelled spheroidenes.- References.- VII: Technical Syntheses.- A. Economic Importance.- 1. Sales.- 2. Areas of application.- B. Industrial Carotenoid Syntheses not involving any Wittig Olefination.- 1. Carotenoid synthons from the Roche synthesis of vitamin A.- 2. ?,?-Carotene.- 3. Apo-?-carotenoids.- 4. Xanthophylls.- C. Industrial Carotenoid Syntheses by means of Wittig Olefination.- 1. Carotenoid building blocks from the BASF synthesis of vitamin A.- 2. ?,?-Carotene.- 3. Apo-?-carotenoids.- 4. Xanthophylls.- D. Formulation.- 1. Colouration of lipophilic media.- 2. Colouration of hydrophilic media – Production of bioavailable preparations.- References.- VIII: Partial Synthesis of Glycosides and Glycosyl Esters.- A. Carotenoid Glycosides.- B. Carotenoid Glycosyl Esters.- References.- IX: Partial Synthesis of Sulphates.- A. Introduction.- B. General Route.- C. Synthesis of Stable Carotenoid Sulphates.- D. Synthesis of Less Stable Carotenoid Sulphates.- E. Preparation and Solvolysis Reactions of Unstable Carotenoid Sulphates.- F. Properties of Carotenoid Sulphates.- References.- Worked Examples.- Example 1: Enol Ether Condensation.- A. Introduction.- B. Examples.- References.- Example 2: Organometallic Reactions.- A. Introduction.- B. Synthesis of Ethynyl-?-ionol.- C. Synthesis of Vinyl-?-ionol.- D. Synthesis of (Z)-?-Ionylideneacetic Acid.- References.- Example 3: Wittig and Horner-Emmons Reaction.- A. Introduction.- B. Syntheses of ?-Apo-8?-carotenoic acid ethyl esters.- References.- Example 4: Sulphone Coupling.- A. Retinoic Acid by the Alkylation-Desulphonylation Method.- B. (all-E)-Retinyl Acetate by the Double Elimination Method.- References.- Example 5: Asymmetric Syntheses.- Asymmetric Epoxidation.- Asymmetric Dihydroxylation.- References.- Example 6: Synthesis ex Chiral Pool.- A. Introduction.- B. Examples.- References.- Example 7: Optical Resolution of Racemic ?-Ionone.- A. Introduction.- B. Synthesis of (R)-(+)-?-Ionone.- Example 8: ?,?-Carotene.- A. Introduction.- B. Synthesis of ?,?-Carotene by use of the Wittig Reaction.- C. Synthesis of ?,?-Carotene by use of Low-valent Titanium.- Appendix I: List of Synthons.- Appendix II: List of Naturally Occurring Carotenoids Prepared by Total Synthesis.- List of abbreviations.

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