Journal
ORGANIC LETTERS
Volume 18, Issue 17, Pages 4348-4351Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02105
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- provincial government of Quebec (FQRNT)
- provincial government of Quebec (CCVC)
- Programme Canadien de Bourses de la Francophonie
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Concise preparations of elaborated polycyclic and heterocyclic systems present in natural products were obtained using the nosyl group as a functional protecting group not only to mask the reactivity of a sensitive moiety but also to provide a structure desired in the final target. The group is transferred to the substrate during deprotection through a novel extension of the Truce Smiles rearrangement in tandem with a 1,4-addition. This strategy provides access to a ring system laden with valuable functionalities for subsequent manipulations and can serve as a versatile building block for the construction of more complex molecular architectures such as indoles in a manner compatible with the concepts of green chemistry and atom economy.
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