Table 7.
Marine natural product structural revisions of single stereocenters (2005–2010).a
| Proposed Structure | Initial Structure Determination Method | Revised Structure | Structure Revision Method |
|---|---|---|---|
 Carriebowmide53 (2008) Cyanobacterium |
Marfey’s |
|
Marfey’s54 |
 Bisebromoamide55(2009) Cyanobacterium |
Marfey’s |
|
Total Synthesis56 |
 Callipeltin E57(2002) Sponge |
Marfey’s |
|
Total Synthesis58 |
 Brevenal61 (2005) Dinoflagellate |
NOE |
|
Total Synthesis62 |
 Solandelactone A63 (1996) Hydrozoan |
HMQC COSY Comparison NOE |
|
Total Synthesis64 |
 Solandelactone B63 (1996) Hydrozoan |
Comparison NOE |
|
Total Synthesis64 |
 Solandelactone C63 (1996) Hydrozoan |
Comparison NOE |
|
Total Synthesis64 |
 Solandelactone D63 (1996) Hydrozoan |
Comparison NOE |
|
Total Synthesis64 |
 Solandelactone E63 (1996) Hydrozoan |
Comparison NOE |
|
Total Synthesis64 |
 Solandelactone F63 (1996) Hydrozoan |
Comparison NOE |
|
Total Synthesis64 |
 Solandelactone G63 (1996) Hydrozoan |
Comparison NOE |
|
Total Synthesis64 |
 Solandelactone H63 (1996) Hydrozoan |
Comparison NOE |
|
Total Synthesis64 |
 Ritterazine B65(1995) Tunicate |
NOE Comparison |
|
Partial Synthesis66 |
 Ritterazine F67(1995) Tunicate |
NOE Comparison |
|
Partial Synthesis66 |
 Netamine E68 (2006) Sponge |
NOE |
|
Total Synthesis69 |
 Netamine G68 (2006) Sponge |
NOE |
|
Total Synthesis69 |
 Briarellin J70 (2003) Coral |
NOESY |
|
Total Synthesis71 |
 Dictyosphaeric acid A72(2004) Fungus |
NOE |
|
Total Synthesis73 |
 Manzacidin B74(1991) Sponge |
J-based Comparison |
|
Total Synthesis75 |
 Agelasine C76 (1984) Sponge |
CD Comparison NMR |
|
Total Synthesis77 |
 Epi-agelasine C78(1984) Sponge |
CD Comparison NMR |
|
Total Synthesis77 |
 Peyssonol A79 (1994) Red alga |
13C NMR |
|
Total Synthesis80 |
 Isoepitaondiol81 (1992) Brown alga |
Comparison |
|
X-ray82 |
 Suberoretisteroid B83 (2000) Gorgonian |
1H NMR |
|
NMR Comparison84 |
 Lanostane-type triterpenoid85(1994) Green alga |
Comparison |
|
X-ray NMR86 |
 Amphidinolide W87 (2002) Dinoflagellate |
Derivatization J-based Mosher |
|
Total Synthesis88 |
 Aspergillide A89(2008) Fungus |
Mosher’s NOE |
|
X-ray90 |
 Aspergillide B89 (2008) Fungus |
Mosher’s NOE |
|
Total Synthesis91, 92 X-ray90 |
 Schulzeine A93 (2004) Sponge |
Deriv. Comparison |
|
Total Synthesis94 |
 Amphidinol 3186 (1999) Dinoflagellate |
Ozonolysis Derivatization Chiral HPLC |
|
Combinatorial synthesis of fragments187 |
 Gymnangiamide188 (2004) Hydrozoan |
Degradation Deriv. Marfey’s |
|
Total Synthesis189 |
 Tridachiahydropyrone190 (1996) Mollusk |
NOE |
|
Total Synthesis191 |
 dihydrodiscorhabdin A192 (2009) Sponge |
J-based Mol. Mod. |
|
CD Semi-synthesis193 |
 Obtusallene V135 (2000) Red alga |
Mol. Mod. NMR Comparison |
|
13C Predict.136 |
 Obtusallene VI135(2000) Red alga |
Mol. Mod. NMR Comparison |
|
13C Predict.136 |
 Obtusallene VII135 (2000) Red alga |
Mol. Mod. NMR Comparison |
|
13C Predict.136 |
 2-formamido-6-axene194 (1989) Sponge |
NOE |
|
NOE Comparison195 |
 Isothiocyanato-6-axene194(1989) Sponge |
NOE |
|
NOE Deriv.195 |
 Obyanamide196 (2002) Cyanobacterium |
Degradation Chromatog. |
|
Total Synthesis197 |
 Dragonamide198(2001) Cyanobacterium |
Degradation OR |
|
Total Synthesis199 |
 Oxazinin-2200(2001) Mussel |
ROESY |
|
Total Synthesis201 |
 Oxazinin-1200(2001) Mussel |
ROESY |
|
Comparison201 |
 Papuamide B202(1999) Sponge |
Degradation Chromatog. |
|
Total Synthesis203 |
a
The year in which the initial structure was published is in parentheses. Only the structure determination methods used for the portion of the structure that is erroneous are mentioned in this table. Predict. = predictions based on molecular modeling. Mol. Mod. = use of geometry optimized structure. Deriv. = derivatization. Chromatog. = chiral HPLC or GC with or without derivatization.