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Synthetic studies on the phorboxazoles: a short synthesis of an epi-C23 tetrahydropyran core

✍ Scribed by Paul A. Clarke; Jason M. Hargreaves; Daniel J. Woollaston; Rosa María Rodríguez Sarmiento

Book ID
104098049
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
386 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

Studies on the synthesis of the anticancer natural products, the phorboxazoles, have led to the synthesis of the C21-C32 penta-substituted tetrahydropyran core which is epimeric to the natural product at C23. The synthesis was achieved in only seven linear steps. The key steps were the use of a Masamune-Abiko anti-aldol reaction, the formation of a dihydropyran precursor molecule by the use of a new 'Maitland-Japp-like' cyclisation, and a highly diastereoselective reductive alkylation of the dihydropyran double bond, to generate the corresponding tetrahydropyran ring in an excellent yield.

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