Integrated Chemical Process: An Extremely Concise Synthesis of Vitamin A

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 7, 1997, Pages 779-780

  Orita, Akihiro ^a   Yamashita, Yasuo ^a   Toh, Akiji ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Eliminations; One pot reactions; Vitamins

Indexed keywords

EID: 0030811719     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199707791     Document Type: Article

References (13)

1. G. H. Posner, Chem. Rev. 1986, 86, 831 ; L. F. Tieze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; a special issue on this subject (Ed.: P. A. Wender): Chem. Rev. 1996, 96, no. 1.
2. G. H. Posner, Chem. Rev. 1986, 86, 831 ; L. F. Tieze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; a special issue on this subject (Ed.: P. A. Wender): Chem. Rev. 1996, 96, no. 1.
3. G. H. Posner, Chem. Rev. 1986, 86, 831 ; L. F. Tieze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; a special issue on this subject (Ed.: P. A. Wender): Chem. Rev. 1996, 96, no. 1.
4. G. H. Posner, Chem. Rev. 1986, 86, 831 ; L. F. Tieze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; a special issue on this subject (Ed.: P. A. Wender): Chem. Rev. 1996, 96, no. 1.
5. Hudlicky pointed out that "a multistep synthesis must therefore be considered as a dynamic continuum in which every event depends on all others": T. Hudlicky, Chem. Rev. 1996, 96, 3.
6. a) T. Mandai, T. Yanagai, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670:
7. b) J. Otera, H. Misawa, T. Mandai, T. Onishi, S. Suzuki, Y. Fujita, Chem. Lett. 1985, 1883;
8. J. Otera, H. Misawa, T. Onishi, S. Suzuki, Y. Fujita, J. Org. Chem. 1986, 51, 3834;
9. J. Otera in Carotenoids, Vol. 2 (Eds.: G. Britton, S. Liaaen-Jensen, H. Pfander), Birkhäuser, Basel, 1996, pp. 103, 311.
10. Note that the yield of step 3 (78%) should come from the successive high-yielding elimination reactions (2 × 88%).
11. J. Paust, Pure Appl. Chem. 1991, 63, 45; J. Paust in Carotenoids, Vol. 2(Eds.: G. Britton, S. Liaaen-Jensen, H. Pfander), Birkhäuser, Basel, 1996, p. 259.
12. J. Paust, Pure Appl. Chem. 1991, 63, 45; J. Paust in Carotenoids, Vol. 2(Eds.: G. Britton, S. Liaaen-Jensen, H. Pfander), Birkhäuser, Basel, 1996, p. 259.
13. Of course, accessibility of the key building blocks is an important factor for assessing the overall brevity of the process. A more detailed discussion will be given in a full paper.