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Organometallic Chemistry can Simplify the Synthesis of Important Biologically Active Natural Products [and Discussion]

D. Becker, P. Carter, J. Elliott, R. Lewis, P. D. Magnus, L. Principe, M. Slater, B. T. Golding and A. B. Holmes
Philosophical Transactions of the Royal Society of London. Series A, Mathematical and Physical Sciences
Vol. 326, No. 1592, The Influence of Organometallic Chemistry on Organic Synthesis: Present and Future (Nov. 3, 1988), pp. 641-651
Published by: Royal Society
Stable URL: http://www.jstor.org/stable/38035
Page Count: 11
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Organometallic Chemistry can Simplify the Synthesis of Important Biologically Active Natural Products [and Discussion]
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Abstract

The stereoselectivity of the Pauson--Khand reaction used for the construction of a 6a-carboprostaglandin is described, and a mechanistic hypothesis is proposed to explain the experimentally observed results. A further illustration of the stereoselectivity of the dicobaltoctacarbonyl-mediated cyclization of 1,6-enynes to bicyclo[3.3.0]-octenones is provided by a sequence of transformations that depicts the route to the precursors of pentalenolactone G. Further examples of the synthetic potential of the acetylene-Co2(CO)6 bimetalloclusters are shown by the synthesis of a vincristine model compound, and a sequence of transformations that provide strong evidence of the intermediacy of a 1,4-diyl (p-benzyne) in the collapse of a Z-diynene to an aromatic product.

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