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- W1498961405 abstract "This chapter details a synthesis of ilimaquinone that led to develop a new strategy and demonstrate further the synthetic applicability of the underexplored Barton's radical decarboxylation. It also discusses the way primary and secondary carbon radicals can react with quinines to form addition products in effective to excellent yields. This addition reaction is characterized by a well-chemoselectivity, taking place only at conjugated and unsubstituted double bonds, and regioselectivity, being influenced by the resonance effect of heteroatoms located on the quinone ring. The evaluation of the scope and limitations of this method allows devising and executing a unified synthesis of several quinone sesquiterpenes. A characteristic of this strategy is that the quinone unit is attached onto a fully functionalized decalin ring toward the end of the synthesis. As such, it is applicable to a parallel synthesis of these and related compounds and provides a new alternative to the previously known synthetic strategy for related molecules." @default.
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- W1498961405 date "2004-01-01" @default.
- W1498961405 modified "2023-09-27" @default.
- W1498961405 title "Chapter 4 Quinone sesquiterpenes: A challenge for the development of a new synthetic methodology" @default.
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- W1498961405 doi "https://doi.org/10.1016/s1874-6004(04)80027-3" @default.
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