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Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes.

ABSTRACT: In the realm of natural product chemistry, few isolates have risen to the level of fame justifiably accorded to Taxol (1) and its chemical siblings. This report describes the most concise route to date for accessing the highly oxidized members of this family. As representative members of taxanes containing five oxygen atoms, decinnamoyltaxinine?E (2) and taxabaccatin?III (3), have succumbed to enantioselective total synthesis for the first time in only 18 steps from a simple olefin starting material. The strategy holistically mimics nature's approach (two-phase synthesis) and features a carefully choreographed sequence of stereoselective oxidations and a remarkable redox-isomerization to set the key trans-diol present in 2 and 3. This work lays the critical groundwork necessary to access even higher oxidized taxanes such as 1 in a more practical fashion, thus empowering a medicinal chemistry campaign that is not wedded to semi-synthesis.

SUBMITTER: Yuan C

PROVIDER: S-EPMC4972021 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes.

Yuan Changxia C Jin Yehua Y Wilde Nathan C NC Baran Phil S PS

Angewandte Chemie (International ed. in English) 20160530 29

In the realm of natural product chemistry, few isolates have risen to the level of fame justifiably accorded to Taxol (1) and its chemical siblings. This report describes the most concise route to date for accessing the highly oxidized members of this family. As representative members of taxanes containing five oxygen atoms, decinnamoyltaxinine E (2) and taxabaccatin III (3), have succumbed to enantioselective total synthesis for the first time in only 18 steps from a simple olefin starting mate ...[more]

PMID: 27240325

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