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Synthesis 1997; 1997(8): 877-885
DOI: 10.1055/s-1997-1278
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Enantioselective Synthesis of Chromans for the Preparation of Enantiopure Vitamin E and Analogues

Lutz F. Tietze* , Jochen Görlitzer
  • *Institut für Organische Chemie der Georg-August Universität, Tammannstrasse 2, D-37077 Göttingen, Germany, Fax +49(551)399476; E-mail: ltietze@gwdg.de
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Publication Date:
31 December 2000 (online)

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Coupling of the different protected (hydroxymethyl)enynes 11a-e and 12a-c with the iodoarene 7 in the presence of catalytic amounts of Pd(PPh3)4 afforded the arylenynes 5a-e and 6a-c which were transformed into the monoprotected chiral trihydroxy compounds 13a-d and 14a,b by Sharpless bishydroxylation with >95% ee for 13a-d, 91% ee for 14b and 64% ee for 14a. A 5-step transformation of 13a led to the desired chroman derivative 3a which was cleaved to give the aldehyde 2 a known precursor for the enantioselective synthesis of vitamin E.

vitamin E - Sharpless bishydroxylation - enynes - palladium - chroman