Chapter

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Volume 39 of the series Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products pp 1-61

Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products

  • B. Fraser-ReidAffiliated withGuelph-Waterloo Centre for Graduate Work in Chemistry, University of Waterloo
  • , R. C. AndersonAffiliated withGuelph-Waterloo Centre for Graduate Work in Chemistry, University of Waterloo

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Abstract

Traditionally, carbohydrate derivatives have been utilized in the mainstream of organic chemistry primarily for studies relating to stereochemical and conformational problems. This is not surprising since these aspects have always been a prime area of concern to sugar chemists because of the role they play in the reactions of sugars. Indeed it was in this connection that the term “conformation” was coined by Haworth in 1929 (34). The work of Barton and Hassell in the late 1940’s on the development of conformational analysis of six membered rings is, of course, well known. However, even prior to this, Reeves had begun his systematic work on the shapes of sugar molecules in solution (78, 79), and it was further concern with the latter that led Lemieux to undertake an examination of sugar acetates by 1H n. m. r. (pmr) spectroscopy in 1957 (53). Thus n. m. r. spectroscopy as practiced in organic chemistry today, owes its origins and much of its early development (54) to the availability of a wealth of well characterized sugar derivatives. 13C n. m. r. (cmr) spectroscopy is similarly indebted (74).