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Publicly Available Published by De Gruyter January 1, 2009

Noniterative approach to the total asymmetric synthesis of 15-carbon polyketides and analogs with high stereodiversity

  • Pierre Vogel , Sandrine Gerber-Lemaire , Ana T. Carmona , Kai Torsten Meilert and Marc-Etienne Schwenter


Starting from inexpensive furan and furfuryl alcohol, a noniterative approach to the synthesis of pentadeca-1,3,5,7,9,11,13,15-octols and their derivatives has been developed. The method relies upon the double [4+3]-cycloaddition of 1,1,3-trichloro-2-oxylallyl cation with 2,2'-methylenedifuran and conversion of the adducts into meso and (±)-threo-1,1'-methylenebis (cis- and trans-4,6-dihydroxycyclohept-1-ene) derivatives. The latter undergo oxidative cleavage of their alkene moieties, generating 5-hydroxy-7-oxoaldehydes that are reduced diastereoselectively into either syn or anti-5,7-diols. Asymmetry is realized using either chiral desymmetrization with Sharpless asymmetric dihydroxylation or by kinetic resolution of polyols using lipase-catalyzed acetylations. All of the possible stereomeric pentadeca-1,3,5,7,9,11,13,15-octols and derivatives can be obtained with high stereoselectivity applying simple operations, thus demonstrating the high stereodiversity of this new, noniterative approach to the asymmetric synthesis of long-chain polyketides.


International Symposium on the Chemistry of Natural Products and the 4th International Congress on Biodiversity, International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 24th, Delhi, India, 2004-01-26–2004-01-31

Published Online: 2009-01-01
Published in Print: 2005-01-01

© 2013 Walter de Gruyter GmbH, Berlin/Boston

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