Recent Advances in the Synthesis of K-Vitamins
The term «Vitamin K» is a collective name and embraces a whole series of 2-methyl-1,4- naphthoquinone derivatives which play a decisive part in the control of blood clotting. The most important representative, vitamin K1 (phylloquinone), has a phytyl group as substituent in the 3-position. On the o...
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Swiss Chemical Society
1986-09-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9744 |
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| author | August Rüttimann |
| author_facet | August Rüttimann |
| author_sort | August Rüttimann |
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The term «Vitamin K» is a collective name and embraces a whole series of 2-methyl-1,4- naphthoquinone derivatives which play a decisive part in the control of blood clotting. The most important representative, vitamin K1 (phylloquinone), has a phytyl group as substituent in the 3-position. On the other hand, K2-vitamins (menaquinones) possess polyunsaturated, isoprenoid side-chains of varying length in this position. – The first technical syntheses of vitamin K. were accomplished by Isler (F. Hoffmann-La Roche & Co. Ltd.) and Hirschmann (Merck & Co. INC., Research Laboratories) more than thirty years ago. In analogy to Fieser’s early work, a protected menadiol is reacted with isophytol or phytol in a Friedel-Crafts type alkylation and vitamin K1 is obtained as a mixture of E- and Z-isomers. – However, biological investigations on vitamin K deficient chicks have clearly indicated that the Z-isomer has virtually no vitamin K activity. In addition, the large number of reaction steps make these syntheses rather unattractive in terms of economy. Therefore, the design of a highly stereoselective and economical synthesis of (E)-vitamin K, has received increasing attention during the last decade; in particular, methodology had to be developed for an efficient coupling of the (E)-phytyl side-chain with the naphthoquinone ring with full retention of the trans double bond.
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| format | Article |
| id | doaj-art-6301d251cef4409a825c78593d7f8aee |
| institution | OA Journals |
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| language | deu |
| publishDate | 1986-09-01 |
| publisher | Swiss Chemical Society |
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| series | CHIMIA |
| spelling | doaj-art-6301d251cef4409a825c78593d7f8aee2025-08-20T01:47:43ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241986-09-0140910.2533/chimia.1986.290Recent Advances in the Synthesis of K-VitaminsAugust Rüttimann0Department of Vitamin and Nutritional Research F. Hoffmann-La Roche & Co. Ltd. Grenzacherstrasse CH4002 Basel The term «Vitamin K» is a collective name and embraces a whole series of 2-methyl-1,4- naphthoquinone derivatives which play a decisive part in the control of blood clotting. The most important representative, vitamin K1 (phylloquinone), has a phytyl group as substituent in the 3-position. On the other hand, K2-vitamins (menaquinones) possess polyunsaturated, isoprenoid side-chains of varying length in this position. – The first technical syntheses of vitamin K. were accomplished by Isler (F. Hoffmann-La Roche & Co. Ltd.) and Hirschmann (Merck & Co. INC., Research Laboratories) more than thirty years ago. In analogy to Fieser’s early work, a protected menadiol is reacted with isophytol or phytol in a Friedel-Crafts type alkylation and vitamin K1 is obtained as a mixture of E- and Z-isomers. – However, biological investigations on vitamin K deficient chicks have clearly indicated that the Z-isomer has virtually no vitamin K activity. In addition, the large number of reaction steps make these syntheses rather unattractive in terms of economy. Therefore, the design of a highly stereoselective and economical synthesis of (E)-vitamin K, has received increasing attention during the last decade; in particular, methodology had to be developed for an efficient coupling of the (E)-phytyl side-chain with the naphthoquinone ring with full retention of the trans double bond. https://www.chimia.ch/chimia/article/view/9744 |
| spellingShingle | August Rüttimann Recent Advances in the Synthesis of K-Vitamins CHIMIA |
| title | Recent Advances in the Synthesis of K-Vitamins |
| title_full | Recent Advances in the Synthesis of K-Vitamins |
| title_fullStr | Recent Advances in the Synthesis of K-Vitamins |
| title_full_unstemmed | Recent Advances in the Synthesis of K-Vitamins |
| title_short | Recent Advances in the Synthesis of K-Vitamins |
| title_sort | recent advances in the synthesis of k vitamins |
| url | https://www.chimia.ch/chimia/article/view/9744 |
| work_keys_str_mv | AT augustruttimann recentadvancesinthesynthesisofkvitamins |