The Absolute Configuration for Inthomycin C: Revision of Previously Published Work with a Reinstatement of the (3R)-Configuration for (-)-Inthomycin C

Karl J. Hale, Susumi Hatakeyama, Fumiya Urabe, Jun Ishihara, Soraya Manaviazar, Milosz Grabski, Maciej Maczka

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Abstract

Abstract Image

Stereochemical evidence is presented to demonstrate that (−)-inthomycin C has (3R)- and not (3S)-stereochemistry. Careful reappraisal of the previously published work2−5 now indicates that the Hatakeyama, Hale, Ryu, and Taylor teams all have synthesized (−)-(3R)-inthomycin C. The newly measured [α]D of pure (−)-(3R)-inthomycin C (98% ee) is −7.9 (c 0.33, CHCl3) and not −41.5 (c 0.1, CHCl3) as was previously reported in 2012.
Original languageEnglish
Pages (from-to)3536-3539
Number of pages4
JournalOrganic Letters
Volume16
Issue number13
Early online date24 Jun 2014
DOIs
Publication statusPublished - 2014

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