Cholesterol total synthesis in chemistry describes the total synthesis of the complex biomolecule cholesterol and is considered a great scientific achievement.[1] The research group of Robert Robinson with John Cornforth (Oxford University) published their synthesis in 1951 [2] and that of Robert Burns Woodward with Franz Sondheimer (Harvard University) in 1952.[3] Both groups competed for the first publication since 1950 with Robinson having started in 1932 and Woodward in 1949. According to historian Greg Mulheirn the Robinson effort was hampered by his micromanagement style of leadership and the Woodward effort was greatly facilitated by his good relationships with chemical industry. Around 1949 steroids like cortisone were produced from natural resources but expensive. Chemical companies Merck & Co. and Monsanto saw commercial opportunities for steroid synthesis and not only funded Woodward but also provided him with large quantities of certain chemical intermediates from pilot plants. Hard work also helped the Woodward effort: one of the intermediate compounds was named Christmasterone as it was synthesized on Christmas Day 1950 by Sondheimer.
Other cholesterol schemes have also been developed: racemic cholesterol was synthesized in 1966 by W.S. Johnson,[4] the enantiomer of natural cholesterol was reported in 1996 by Rychnovsky and Mickus,[5] in 2002 by Jiang & Covey [6] and again in 2008 by Rychnovsky and Belani.[7]
^Robinson, Woodward and the synthesis of cholesterol Greg Mulheirn Endeavour Volume 24, Issue 3, 1 September 2000, Pages 107-110 doi:10.1016/S0160-9327(00)01310-7
^Cardwell, H. M. E., Cornforth, J. W., Duff, S. R., Holtermann, H ,Robinson, Robert, Chemistry & Industry, 1951, 389-90
^The Total Synthesis of Steroids R. B. Woodward, Franz Sondheimer, David Taub, Karl Heusler, W. M. McLamore J. Am. Chem. Soc., 1952, 74 (17), pp. 4223–4251 doi:10.1021/ja01137a001
^Steroid total synthesis—hydrochrysene approach—XVI: Racemic conessine, progesterone, cholesterol, and some related natural products W. S. Johnson, J. A. Marshall, J. F. W. Keana, R. W. Franck, D. G. Martin and J. V. Bauer Tetrahedron Volume 22, Supplement 8, 1966, Pages 541-601 doi:10.1016/S0040-4020(01)90961-5
^Synthesis of ent-cholesterol, the unnatural enantiomer Scott D. Rychnovsky, Daniel E. Mickus J. Org. Chem., 1992, 57 (9), pp. 2732–2736 doi:10.1021/jo00035a036
^Total Synthesis of ent-Cholesterol via a Steroid C,D-Ring Side-Chain Synthon Xin Jiang and Douglas F. Covey J. Org. Chem., 2002, 67 (14), pp. 4893–4900 doi:10.1021/jo025535k
^A Concise Synthesis of ent-Cholesterol Scott D. Rychnovsky, Jitendra D. Belani J. Org. Chem., 2008, 73 (7), pp. 2768–2773 doi:10.1021/jo702694g
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