Straight-Ahead Synthesis

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Science  19 Dec 2008:
Vol. 322, Issue 5909, pp. 1758-1759
DOI: 10.1126/science.322.5909.1758d

One regrettably common source of inefficiency in the synthesis of complex organic molecules is the need to apply successive oxidation-reduction cycles. In principle, a synthesis could proceed by preparing fragments of the molecule in more or less final form and then linking them together in the proper order. In practice, however, this strategy often leaves dangling groups in the wrong orientation or fails to provide reliable linkage sites at intermediate stages. Fragments incorporated into the partial framework must then be modified, often through redox transformations, to facilitate further assembly, after which they must somehow be retransformed into their previous, proper state. Nicewicz et al. have skirted this dilemma in the assembly of the intricately oxygenated core of zaragozic acid C. Taking advantage of a silyl glyoxylate reagent that can self-couple by acting successively as an electrophile and nucleophile, the authors built up the core through several straightforward carbon-carbon bond-forming steps. They could then complete the overall construction of the molecule with minimal application of redox modifications, highlighting the potential of the approach for general synthetic efficiency. — JSY

J. Am. Chem. Soc. 10.1021/ja808347q (2008).

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