Publikation: Total synthesis of the complex taxane diterpene canataxpropellane
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2020
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Science. American Association for the Advancement of Science (AAAS). 2020, 367(6478), pp. 676-681. ISSN 0036-8075. eISSN 1095-9203. Available under: doi: 10.1126/science.aay9173
Zusammenfassung
Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C-C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (-)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (-)-canataxpropellane (2) was assembled in two steps using a Diels-Alder/ortho-alkene-arene photocycloaddition sequence. Enantioselectivity was introduced by designing chiral siloxanes to serve as auxiliaries in the Diels-Alder reaction.
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SCHNEIDER, Fabian, Konstantin SAMARIN, Simone ZANELLA, Tanja GAICH, 2020. Total synthesis of the complex taxane diterpene canataxpropellane. In: Science. American Association for the Advancement of Science (AAAS). 2020, 367(6478), pp. 676-681. ISSN 0036-8075. eISSN 1095-9203. Available under: doi: 10.1126/science.aay9173BibTex
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year={2020},
doi={10.1126/science.aay9173},
title={Total synthesis of the complex taxane diterpene canataxpropellane},
number={6478},
volume={367},
issn={0036-8075},
journal={Science},
pages={676--681},
author={Schneider, Fabian and Samarin, Konstantin and Zanella, Simone and Gaich, Tanja}
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<dcterms:abstract xml:lang="eng">Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C-C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (-)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (-)-canataxpropellane (2) was assembled in two steps using a Diels-Alder/ortho-alkene-arene photocycloaddition sequence. Enantioselectivity was introduced by designing chiral siloxanes to serve as auxiliaries in the Diels-Alder reaction.</dcterms:abstract>
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