Corrigendum to "study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide e and 6-hydroxydeoxybrevianamide E" [Tetrahedron Lett. 52 (2011) 6923-6926]

Full text of DOI:10.1016/j.tetlet.2013.11.076

Tetrahedron Letters 55 (2014) 559–560
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Tetrahedron Letters
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Corrigendum
Corrigendum to ‘‘Study on the biosynthesis of the notoamides:
pinacol-type rearrangement of the isoprenyl unit in
deoxybrevianamide E and 6-hydroxydeoxybrevianamide E’’
[Tetrahedron Lett. 52 (2011) 6923–6926]
Hikaru Kato a, Yuichi Nakamura a, Jennifer M. Finefield b, Hideharu Umaoka a, Takashi Nakahara a,
Robert M. Williams b,c, , Sachiko Tsukamoto a,
⇑
⇑
a Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
b Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, CO 80523, USA
c University of Colorado Cancer Center, Aurora, CO 80045, USA
The structures of the synthetic, unlabeled compounds 10 and 16 shown in page S11 of the Supporting Information section were incor-
rectly reported. The correct structures for 10 and 16 are as follows:
This is due to the absence of the third oxindole carbonyl resonance. The synthetic isotopically labeled compounds are also incorrectly
assigned and the scheme on page S9 of the Supporting Information should be corrected as follows:
With these corrections, structures on pages S10 and S12 also should be corrected.
The structures of the labeled isolated metabolites 10 and 16 in the feeding experiment of isotopically labeled 7 were determined based
on their 1H NMR spectra of synthetic 10 and 16 as shown in Figure 3. Therefore, accompanied by the above correction, the labeled metab-
olites 10 and 16 from 7 in Figure 3 of the Letter should be corrected as follows:
q DOI of original article: http://dx.doi.org/10.1016/j.tetlet.2011.10.065
⇑
Corresponding authors.
E-mail address: sachiko@kumamoto-u.ac.jp (S. Tsukamoto).
0040-4039/$ - see front matter Ó 2013 Elsevier Ltd. All rights reserved.
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H. Kato et al. / Tetrahedron Letters 55 (2014) 559–560
The absolute configuration of 14 in Figure 3 should be corrected as follows:
This error was caused by the configuration of notoamide C, which was initially assigned as 3R based on biogenetic considerations.1 Re-
cently, the absolute configuration of notoamide C was corrected to be 3S based on the biochemical conversion of notoamide E into notoa-
mide C by recombinant NotB.2 Accordingly, the configuration of 3-epi-notoamide C was corrected to be 3R. Since the CD spectrum of 14 was
identical to that of 3-epi-notoamide C,3 the configuration of 14 should be also corrected to 3R. Recently, the relative and absolute config-
uration of notoamide C was independently reported by Chen et al. by single crystal X-ray analysis of notoamide C isolated from Aspergillus
sp. XS-20090066.5
Versicolamide B, isolated from the marine-derived Aspergillus sp. and assigned to be (À)-enantiomer,4 was corrected to (+)-enantiomer.
This mistake affects Figure 4 and text in right column on page 6925.
References and notes
1. Kato, H.; Yoshida, T.; Tokue, T.; Nojiri, Y.; Hirota, H.; Ohta, T.; Williams, R. M.; Tsukamoto, S. Angew. Chem., Int. Ed. 2007, 46, 2254–2256.
2. Li, S.; Finefield, J. M.; Sunderhaus, J. D.; McAfoos, T. J.; Williams, R. M.; Sherman, D. H. J. Am. Chem. Soc. 2012, 134, 788–791.
3. Tsukamoto, S.; Umaoka, H.; Yoshikawa, K.; Ikeda, T.; Hirota, H. J. Nat. Prod. 2010, 73, 1438–1440.
4. Tsukamoto, S.; Kawabata, T.; Kato, H.; Greshock, T. J.; Hirota, H.; Ohta, T.; Williams, R. M. Org. Lett. 2009, 11, 1297–1300.
5. Chen, M.; Shao, C.-L.; Fu, X.-M.; Xu, R.-F.; Zheng, J.-J.; Zhao, D.-L.; She, Z.-G.; Wang, C.-Y. J. Nat. Prod. 2013, 76, 547–553.