A nucleophilic addition ring closure [NARC]-based synthesis of (+) -nonactic acid

Ben Fraser, Patrick Perlmutter

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

Abstract

Nonactic acid I has been synthesized in 12 steps from readily available (S)-(-)-Et lactate in 20 overall yield. The key ( NARC ) sequence in this method involved anti-aldol addn. of acylsultam II with aldehyde III followed by intramol. oxymercuration. The efficiency and selectivity of the anti-aldol reaction was found to be critically dependent upon the ratio of Lewis acid to base. The intramol. oxymercuration was also found to be highly diastereoselective and was attributed to allylic control consistent with previous studies in our group. [on SciFinder(R)]
Original languageEnglish
Pages (from-to)2896-2899
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume1
Issue number24
DOIs
Publication statusPublished - 2002

Cite this