proposed biogenetic origin of secu'amamine a from allosecurinine:  a model study to support...

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Additions and Corrections Volume 8, 2006 Philip Magnus* and Angela I. Padilla Proposed Biogenetic Origin of Secu’amamine A from Allosecurinine: A Model Study To Support the Intermediacy of the Putative Aziridinium Ion. Page 3569. In Scheme 2, structure 15 is correct, but the 3D representation contains an extra carbon atom. A corrected scheme is shown below. OL062158F 10.1021/ol062158f Published on Web 09/09/2006 Hirofumi Seike, Indranath Ghosh, and Yoshito Kishi* Stereochemistry of Sagittamide A: Prediction and Confirma- tion. Page 3866. In Figure 2, the 3 J H,H profile of the SAA subgroup in panel D was incorrect. Figure 2 with the correct 3 J H,H profile of the SAA subgroup in panel D is shown below. OL062156V 10.1021/ol062156v Published on Web 09/12/2006 Scheme 2. Analysis of Aziridinium Ion Intermediate Figure 2. Profile analysis of the 3 JH,H coupling constants reported for the C5-C10 moiety of sagittamide A. 1 Panel A: Overall profile re- ported where a, b, c, d, and e represent the vicinal spin-coupling con- stants (Hz) observed for H5/H6, H6/H7, H7/H8, H8/H9, and H9/H10, respectively. Panel B: 3 JH,H profile composed of the three 3 JH,H’s of H7/H8-H8/H9-H9/H10; this profile best matches the SAS profile in Figure 1 (|Hz| ) 0.8 Hz). Panel C: 3 JH,H profile composed of the three 3 JH,H’s of H6/H7-H7/H8-H8/H9; this profile best matches the ASA profile (|Hz| ) 2.1 Hz). Panel D: 3 JH,H profile composed of the three 3 JH,H’s of H5/H6-H6/H7-H7/H8; this profile best matches the SAA profile (|Hz| ) 2.1 Hz). I: predicted relative stereochem- istry of the C5-C10 moiety of sagittamide A. 4 Abbreviations: A ) anti and S ) syn. ORGANIC LETTERS 2006 Vol. 8, No. 22 5177 10.1021/ol062158f CCC: $33.50 © 2006 American Chemical Society Published on Web 09/09/2006

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Page 1: Proposed Biogenetic Origin of Secu'amamine A from Allosecurinine:  A Model Study To Support the Intermediacy of the Putative Aziridinium Ion

Additions and Corrections

Volume 8, 2006

Philip Magnus* and Angela I. Padilla

Proposed Biogenetic Origin of Secu’amamine A fromAllosecurinine: A Model Study To Support the Intermediacyof the Putative Aziridinium Ion.

Page 3569. In Scheme 2, structure15 is correct, but the3D representation contains an extra carbon atom. A correctedscheme is shown below.

OL062158F

10.1021/ol062158fPublished on Web 09/09/2006

Hirofumi Seike, Indranath Ghosh, and Yoshito Kishi*Stereochemistry of Sagittamide A: Prediction and Confirma-tion.

Page 3866. In Figure 2, the3JH,H profile of the SAAsubgroup in panel D was incorrect. Figure 2 with the correct3JH,H profile of the SAA subgroup in panel D is shown below.

OL062156V

10.1021/ol062156vPublished on Web 09/12/2006

Scheme 2. Analysis of Aziridinium Ion Intermediate

Figure 2. Profile analysis of the3JH,H coupling constants reported forthe C5-C10 moiety of sagittamide A.1 Panel A: Overall profile re-ported where a, b, c, d, and e represent the vicinal spin-coupling con-stants (Hz) observed for H5/H6, H6/H7, H7/H8, H8/H9, and H9/H10,respectively.Panel B: 3JH,H profile composed of the three3JH,H’s ofH7/H8-H8/H9-H9/H10; this profile best matches the SAS profile inFigure 1 (∑|∆Hz| ) 0.8 Hz).Panel C: 3JH,H profile composed of thethree3JH,H’s of H6/H7-H7/H8-H8/H9; this profile best matches theASA profile (∑|∆Hz| ) 2.1 Hz).Panel D: 3JH,H profile composed ofthe three3JH,H’s of H5/H6-H6/H7-H7/H8; this profile best matchesthe SAA profile (∑|∆Hz| ) 2.1 Hz).I: predicted relative stereochem-istry of the C5-C10 moiety of sagittamide A.4 Abbreviations: A)anti and S) syn.

ORGANICLETTERS

2006Vol. 8, No. 22

5177

10.1021/ol062158f CCC: $33.50 © 2006 American Chemical SocietyPublished on Web 09/09/2006