Journal
MOLECULES
Volume 20, Issue 1, Pages 1475-1494Publisher
MDPI AG
DOI: 10.3390/molecules20011475
Keywords
hypervalent iodine; ring expansion; rearrangement; seven-membered ring; antiproliferative activity
Funding
- FAPESP [2010/16042-6, 2012/10568-1]
- CAPES
- CNPq
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [12/10568-1] Funding Source: FAPESP
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A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven-and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). Reaction conditions can be easily adjusted to give ring expansion products bearing different functional groups. A route to medium-ring lactones was also developed.
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