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

doi:10.1021/ol501484t

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

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

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 language	English
Pages (from-to)	3536-3539
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	13
Early online date	24 Jun 2014
DOIs	https://doi.org/10.1021/ol501484t
Publication status	Published - 2014

Access to Document

10.1021/ol501484t

http://pubs.acs.org/doi/abs/10.1021/ol501484t

Cite this

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

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.",

author = "Hale, \{Karl J.\} and Susumi Hatakeyama and Fumiya Urabe and Jun Ishihara and Soraya Manaviazar and Milosz Grabski and Maciej Maczka",

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T1 - The Absolute Configuration for Inthomycin C: Revision of Previously Published Work with a Reinstatement of the (3R)-Configuration for (-)-Inthomycin C

AU - Hale, Karl J.

AU - Hatakeyama, Susumi

AU - Urabe, Fumiya

AU - Ishihara, Jun

AU - Manaviazar, Soraya

AU - Grabski, Milosz

AU - Maczka, Maciej

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

U2 - 10.1021/ol501484t

DO - 10.1021/ol501484t

M3 - Article

SN - 1523-7060

VL - 16

SP - 3536

EP - 3539

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -