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By Hanspeter Pfander, Synnøve Liaaen-Jensen, George Britton (auth.), Dr. George Britton, Professor Dr. Dr. h. c. Synnøve Liaaen-Jensen, Professor Dr. Dr. h. c. Hanspeter Pfander (eds.)

ISBN-10: 303489323X

ISBN-13: 9783034893237

ISBN-10: 3034893256

ISBN-13: 9783034893251

George Britton, Synnl/Jve Liaaen-Jensen and Hanspeter Pfander This e-book, quantity 2 within the sequence Carotenoids, is the 1st booklet to be released that's dedicated completely to the entire synthesis of carotenoids, however it is well timed in view of the speedy improvement and the transforming into diversification of the carotenoid box. The 1971 Carotenoids publication contained a big bankruptcy of 250 pages on overall synthesis by way of H. Mayer and O. Isler. That accomplished and authoritative evaluate defined systematically the development of many synthons and the synthesis of many average and unnatural carotenoids and comparable compounds. Twenty 5 years on, that bankruptcy continues to be a necessary reference paintings and resource of knowledge, with its vast number of tabulated information and lists of references to the unique literature. Surveys of growth because 1971 were offered on the IUPAC foreign Symposia on Carotenoids and are integrated within the released lawsuits of those symposia. The heritage of significant guides within the carotenoid box, resulting in the advance of this sequence, used to be defined within the preface to the sequence released in Vol. IA. the final philo­ sophy defined in that preface, with emphasis on functional advice and the inclusion of labored examples of a few of the main precious techniques, is maintained in Vol. 2. In kceping with this philosophy, Vol. 2 isn't meant to be an exhaustive assessment of the literature, yet is deliberate as a realistic e-book, in addition to a resource of information.

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Extra resources for Carotenoids: Volume 2: Synthesis

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R, :! 0 ~ U U u u u u + ~ ill + ::£ L. Labler, A. Riittimann and A. r '" ,(j ( ( ( ( ( ( ~ ~ ~ ~ ~ ~ ~ -" N '"'" N 0 0 0 0 15 ':: 0 Q. ~ N 0 w ~ iij Q. t ,(j 0 ~ iij 15 ,(j Q. " ::;; Q. :"; ::: U U U U U U 0 (3 J 3 u u + + 0 '" + + CS+C3 C3+C4 C, C](l C14 C3+C" C, C 1l+C3 +C3 2 C2+ C] C-' J-o~ ~O~ ~(OEt), (EtO),~(OEt), 5 ~O~ ~O~ ~(OEt), ~(OEt), 7 8 6 ~o""""""'" ~o~ ~o~ ~O~ Enol ether (EtO),~(OEt), Me,C(OEt), MeCH(OEI), CH(OEtj, Cn-Component 4 3 I Cr+C} C4 C n + C, Ex. ZnClz SF, ZnCI 2 SF, ZnCI 2 SF, ZnCI", ZnGI 2 FeCI 3 ZnCI 2 SF, SF, SF, Promoter Table 2: Alkyl enol ether condensation (chain lengthening by C 3 , products as mixed (EIZ)-isomers) r o ~O II O~O 59 59 55 65 53 64 63 46 46 18 62 Ref.

R '" ,(j ( ( ( ( ( ( ~ ~ ~ ~ ~ ~ ~ -" N '"'" N 0 0 0 0 15 ':: 0 Q. ~ N 0 w ~ iij Q. t ,(j 0 ~ iij 15 ,(j Q. " ::;; Q. :"; ::: U U U U U U 0 (3 J 3 u u + + 0 '" + + CS+C3 C3+C4 C, C](l C14 C3+C" C, C 1l+C3 +C3 2 C2+ C] C-' J-o~ ~O~ ~(OEt), (EtO),~(OEt), 5 ~O~ ~O~ ~(OEt), ~(OEt), 7 8 6 ~o""""""'" ~o~ ~o~ ~O~ Enol ether (EtO),~(OEt), Me,C(OEt), MeCH(OEI), CH(OEtj, Cn-Component 4 3 I Cr+C} C4 C n + C, Ex. ZnClz SF, ZnCI 2 SF, ZnCI 2 SF, ZnCI", ZnGI 2 FeCI 3 ZnCI 2 SF, SF, SF, Promoter Table 2: Alkyl enol ether condensation (chain lengthening by C 3 , products as mixed (EIZ)-isomers) r o ~O II O~O 59 59 55 65 53 64 63 46 46 18 62 Ref.

Unsaturated acetal end specifically in the presence of a saturated acetal (Table 1 example 8 and Table 2 example 4). The outcome of the reaction with aromatic and saturated aliphatic acetals can be controlled by using an excess (up to 5: 1) of the starting acetal [6]. The quantitative relative reactivities of acetals have been investigated in detail [8]. CH 0 + '\ R20BF3 OR 2 6 n V 5 OR 4 ~ R3 R2 0 OR 4 7 ~OR' R3 1 R3 tlI - e R'OBF3 ~ 2 e R OBF3 ~ Scheme 2 Rl OR 2 R2 O Y O R 4 R3 8 29 Coupling Reactions: Part I The main advantage of the enol ether condensation, compared with the aldol condensation, is that the enol ether reacts exclusively as the nucleophilic reaction partner and the acetal exclusively as the electrophilic one; this leads unequivocally to the desired, uniform, reaction product.

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Carotenoids: Volume 2: Synthesis by Hanspeter Pfander, Synnøve Liaaen-Jensen, George Britton (auth.), Dr. George Britton, Professor Dr. Dr. h. c. Synnøve Liaaen-Jensen, Professor Dr. Dr. h. c. Hanspeter Pfander (eds.)


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