Nicolaou Taxol total synthesis overview from raw material perspective.
The Nicolaou Taxol total synthesis, published by K. C. Nicolaou and his group in 1994 concerns the total synthesis of taxol.[1] Taxol is an important drug in the treatment of cancer but also expensive because the compound is harvested from a scarce resource, namely the pacific yew.
This synthetic route to taxol is one of several; other groups have presented their own solutions, notably the group of Holton with a linear synthesis starting from borneol, the Samuel Danishefsky group starting from the Wieland-Miescher ketone and the Wender group from pinene.
The Nicolaou synthesis is an example of convergent synthesis because the molecule is assembled from three pre-assembled synthons. Two major parts are cyclohexene rings A and C that are connected by two short bridges creating an 8 membered ring in the middle (ring B). The third pre-assembled part is an amide tail. Ring
D is an oxetane ring fused to ring C. Two key chemical transformations are the Shapiro reaction and the pinacol coupling reaction.[2]
The overall synthesis was published in 1995 in a series of four papers.[3][4][5][6]
^Classics in Total Synthesis: Targets, Strategies, Methods K. C. Nicolaou, E. J. Sorensen ISBN 3-527-29231-4
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K. C. Nicolaou; P. G. Nantermet; H. Ueno; R. K. Guy; E. A. Couladouros & E. J. Sorensen (1995). "Total Synthesis of Taxol. 1. Retrosynthesis, Degradation, and Reconstitution". J. Am. Chem. Soc. 117 (2): 624–633. doi:10.1021/ja00107a006. S2CID 30357150.
^
K. C. Nicolaou; J.-J. Liu; Z. Yang; H. Ueno; E. J. Sorensen; C. F. Claiborne; R. K. Guy; C.-K. Hwang; M. Nakada & P. G. Nantermet (1995). "Total Synthesis of taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system". J. Am. Chem. Soc. 117 (2): 634–644. doi:10.1021/ja00107a007.
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K. C. Nicolaou; Z. Yang; J.-J. Liu; P. G. Nantermet; C. F. Claiborne; J. Renaud; R. K. Guy & K. Shibayama (1995). "Total Synthesis of Taxol. 3. Formation of Taxol's ABC Ring Skeleton". J. Am. Chem. Soc. 117 (2): 645–652. doi:10.1021/ja00107a008.
^
K. C. Nicolaou; H. Ueno; J.-J. Liu; P. G. Nantermet; Z. Yang; J. Renaud; K. Paulvannan & R. Chadha (1995). "Total Synthesis of Taxol. 4. The Final Stages and Completion of the Synthesis". J. Am. Chem. Soc. 117 (2): 653–659. doi:10.1021/ja00107a009.
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