Excerpt from Organic Seminar Abstracts, 1979-80: Semester II

Nature continues to provide a plethora of molecules which, for aesthetic, economic, and medicinal reasons, captures the attentions of synthetic organic chemists. Recently, efforts in many laboratories have focused on targets in the ansamycin, la polyether,1b and macrolide1c anti biotic families; these polyoxygenated molecules are rich in asymmetry and represent a formidable synthetic challenge to the imaginations and current methodologies of chemists. Many of these compounds have acyclic or macro cyclic structures which render them conformationally mobile. While stereo chemical control can be routinely achieved in the synthesis of conforma tionally immobile systems, stereochemical control in synthetic manipulations involving conformationally flexible molecules remains one of the unsolved problems in organic chemistry. The traditional strategy in synthesizing molecules such as these has involved controlling the stereochemistry by using conformationally unambiguous 5 or 6 - membered ring system precursors which can be ultimately opened and incorporated into acyclic or macrocyclic targets. The recent independent syntheses of the prelog-djerassi lactone by Stork2 and White3 and the macrolide syntheses by masamune1c and Corey attest to the power of such an approach. Much interest has been stimulated, however, in the control of stereochemistry in conformationally hetero geneous, acyclic systems. Many investigators have now begun to penetrate this largely unexplored region of organic synthesis and several novel solutions have been advanced. Some of these solutions will be discussed.

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