Erratum: Syntheses of pseudoceramines A-D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges (Organic and Biomolecular Chemistry (2012) 10 DOI: 10.1039/C1OB06722B))

Full text of DOI:10.1039/c2ob90180c

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ADDITIONS & CORRECTIONS
C–H functionalization of tertiary amines by cross dehydrogenative coupling reactions: solvent-free synthesis of
α-aminonitriles and β-nitroamines under aerobic condition
Kaliyamoorthy Alagiri and Kandikere Ramaiah Prabhu
Org. Biomol. Chem., 2012, 10, 835–842 (DOI: 10.1039/C1OB06466E).
The authors regret the following errors:
Table 3, column 2, entries 2–6 are incorrect. MnO2(acac)2 (10) should read as MoO2(acac)2 (10).
“Frustrated Lewis pair” hydrogenations
Douglas W. Stephan
Org. Biomol. Chem., 2012, 10 (DOI: 10.1039/c2ob25339a).
The text on Page 2 of the manuscript Line 43 should read:
Papai’s model (Fig. 1(a)) suggests a linear arrangement of the P-H2-B atoms in the transition state.
N-Fmoc-α-sulfo-β-alanine: a versatile building block for the water solubilisation of chromophores and fluorophores by
solid-phase strategy
Anthony Romieu, Thomas Bruckdorfer, Guillaume Clavé, Virgile Grandclaude, Cédrik Massif and Pierre-Yves Renard
Org. Biomol. Chem., 2011, 9, 5337–5342 (DOI: 10.1039/C1OB05730H).
An error has been made in the calculation of the relative quantum yield of water-soluble naphthalene derivative 11 in PBS at 25 °C
(see Table 1): it should read 2.27 (227%) instead of 0.23 (23%) by using naphthalene in cyclohexane as standard. However, in order
to get a value in the range 0–100%, a further quantum yield determination of 11 has been done with (E)-stilbene in hexane as standard
(Φstd = 0.05). A new value of 0.76 (76%) has been found for 11 in PBS at 25 °C.
The authors regret this unwitting error.
This journal is © The Royal Society of Chemistry 2012
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Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order
molecular assemblies
Oliver Plietzsch, Christine Inge Schilling, Mariyan Tolev, Martin Nieger, Clemens Richert, Thierry Muller and Stefan Bräse
Org. Biomol. Chem., 2009, 7, 4734–4743 (DOI: 10.1039/B912189G).
There was an omission in the experimental procedure for tetrakis(4-azidophenyl)methane (7). The corrected procedure is given below
with the additional text in bold.
Tetrakis(4-azidophenyl)methane (7). 4,4′,4′′,4′′′-Methanetetrayltetraaniline (5) (1.50 g, 3.93 mmol, 1.0 equiv.) was suspended in
water (30 mL) and the reaction mixture was cooled to −5 °C. At this temperature conc. sulfuric acid (15 mL) and a solution of
sodium nitrite (1.23 g, 17.7 mmol, 4.5 equiv.) in water (9 mL) were added slowly and the suspension turned to a dark clear sol-
ution. Then, a solution of sodium azide (1.23 g, 17.7 mmol, 4.5 equiv.) in water (9 mL) was added dropwise under a strong evolution
of gas. Caution: sodium azide is potentially explosive. Furthermore, the evolution of hydrazoic acid is possible under acidic con-
ditions. The reaction mixture was stirred for 2 h at room temperature. After this, the formed precipitate was filtered off, washed with
water (100 mL) and dried in vacuo to give tetrakis(4-azidophenyl)methane (7) (1.43 g, 75%) as a grey solid. Rf 0.30 (cyclohexane/
EtOAc 25 : 1); δH (400 MHz; CDCl3) 6.86 (8 H, d, J 8.8, Arm-H), 7.06 (8 H, d, J 8.8, Aro-H) ppm; δC (100 MHz; CDCl3) 63.3
(Cq(Ar)4), 118.4 (+, Co-Ar), 132.1 (+, Cm-Ar), 138.2 [Cq-Ar(N3)], 142.9 [Cq-Ar(C)] ppm; ν/cm−1 (DRIFT) 3032wv, 2544vw, 2412vw,
2252w, 2124s, 1601m, 1577w, 1501s, 1413w, 1290s, 1192 m, 1130w, 1119w, 1017w, 945vw, 911vw, 829m, 757vw, 701vw, 671w,
634vw, 555m, 538m, 414vw; m/z (EI) 484 (M+, 100%), 456 (35), 317 (M+ − 12N, 12), 240 (M+ − C6H4N12, 9); C25H16N12 calcd
484.1621; found 484.1623 [M+].
Selective thioether macrocyclization of peptides having the N-terminal 2-chloroacetyl group and competing two or three
cysteine residues in translation
Kazuhiro Iwasaki, Yuki Goto, Takayuki Katoh and Hiroaki Suga
Org. Biomol. Chem., 2012, 10 (DOI: 10.1039/C2OB25306B).
The descriptive text in reference 12 has been placed incorrectly. The corrected version is shown below:
12 (a) A. Ohta, H. Murakami, E. Higashimura and H. Suga, Chem. Biol., 2007, 14, 1315–1322; In addition to genetic code reprogram-
ming, a hydroxy acid has been incorporated into amber codon in the following papers: (b) J. A. Ellman, D. Mendel and P. G. Schultz,
Science (Washington, D. C.), 1992, 255, 197–200; (c) P. M. England, H. A. Lester and D. A. Dougherty, Biochemistry, 1999, 38,
14409–14415; (d) S. W. Millward, T. T. Takahashi and R. W. Roberts, J. Am. Chem. Soc., 2005, 127, 14142–14143.
9748 | Org. Biomol. Chem., 2012, 10, 9747–9750
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Syntheses of pseudoceramines A–D and a new synthesis of spermatinamine, bromotyrosine natural products from
marine sponges
J. Mikael Hillgren, Christopher T. Öberg and Mikael Elofsson
Org. Biomol. Chem., 2012, 10 (DOI: 10.1039/C1OB06722B).
There was an error in Scheme 4: the last line was missing. The correct scheme is given below.
Scheme 4 Synthesis of the bromotyrosine building blocks 13 and 14.
This journal is © The Royal Society of Chemistry 2012
Org. Biomol. Chem., 2012, 10, 9747–9750 | 9749

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Rationale for the opposite stereochemistry of the major monoadducts and interstrand crosslinks formed by mitomycin
C and its decarbamoylated analogue at CpG steps in DNA and the effect of cytosine modification on reactivity
Juan A. Bueren-Calabuig, Ana Negri, Antonio Morreale and Federico Gago
Org. Biomol. Chem., 2012, 10, 1543–1552 (DOI: 10.1039/C1OB06675G).
The authors regret that the acknowledgements section was not included in the paper. The section is included below.
Acknowledgements
This work was partially supported by Comisión Interministerial de Ciencia y Tecnología (SAF2006-12713-C02-02 and SAF2009-
13914-C02-02) and Comunidad de Madrid (S-BIO/0214/2006). J.A.B.-C. enjoys a research fellowship from PharmaMar S.A.U. A.M.
acknowledges Comunidad Autónoma de Madrid for financial support through the AMAROUTO program to the Fundación Severo
Ochoa.
We thankfully acknowledge the generous allowance of computer resources, technical expertise and assistance provided by the Red
Española de Supercomputación at the Barcelona Supercomputing Center (MareNostrum). We are grateful to Prof. María José Camar-
asa (IQM, CSIC), Dr Sonsoles Velázquez (IQM, CSIC), Dr Carolina Burgos (UAH) and Prof. Antonio Jiménez-Ruiz (UAH) for many
fruitful discussions.
The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.
Additions and corrections can be viewed online by accessing the original article to which they apply.
9750 | Org. Biomol. Chem., 2012, 10, 9747–9750
This journal is © The Royal Society of Chemistry 2012