Taming of a superbase for selective phenol desilylation and natural product isolation

Darci J. Trader, Erin E. Carlson

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Hydroxyl moieties are highly prevalent in natural products. We previously reported a chemoselective strategy for enrichment of hydroxyl-functionalized molecules by formation of a silyl ether bond to a resin. To generate smaller pools of molecules for analysis, we developed cleavage conditions to promote stepwise release of phenolic silyl ethers followed by aliphatic silyl ethers with a "tamed" version of the superbase 1,1,3,3-tetramethylguanadine. We demonstrate this as a general strategy for selective deprotection of phenolic silyl ethers under neutral conditions at room temperature.

Original languageEnglish (US)
Pages (from-to)7349-7355
Number of pages7
JournalJournal of Organic Chemistry
Volume78
Issue number14
DOIs
StatePublished - Jul 19 2013

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