Synthetic Approaches to the Lamellarins—A Comprehensive Review
Abstract
:1. Introduction
2. Syntheses of type-II Lamellarins
2.1. Fürstner 1995 [65]
2.2. Banwell 1997 [66]
2.3. Boger 1999 [67]
2.4. Álvarez 2004 [68]
2.5. Iwao 2008 [69]
2.6. Jia 2011 [70]
2.7. Vazquez 2012 [71]
3. Syntheses of Type I-Lamellarins—Approaches via Halogenation and Cross-Coupling Reactions
3.1. Iwao 2003 (lamellarin G trimethyl ether) [72]-2006 (lamellarin D, L and N) [73]-2006 (lamellarin α 20‑sulfate) [74]-2010 (lamellarin α 20-sulfate, α 13-sulfate and α 13,20-disulfate) [75]
3.2. Handy 2004 [78]
3.3. Álvarez 2005 [79]
3.4. Banwell 2011 [80]
3.5. Iwao 2014 [81]
4. Syntheses of Type I-lamellarins—Approaches via N-Ylide-Mediated Pyrrole Ring Formation
4.1. Iwao 1997 [82]
4.2. Guitián 2001 [83]
4.3. Ruchirawat 2001 [84]
4.4. Ruchirawat 2004 (lamellarin K&L) [85]-2006 (28 different lamellarins) [86]-Opatz 2008 (lamellarin G trimethyl ether & lamellarin U) [87]
5. Synthesis of type-I Lamellarins—Miscellaneous Approaches
5.1. Banwell 1997 [88]//Faulkner 2002 [89]//Alvarez 2003 [90]
5.2. Steglich 1997 (lamellarin G trimethyl ether) [92]-2000 (lamellarin L) [77]-2006 (lamellarin G & K) [93]-2009 Guptón (Steglich Synthon) [94]
5.3. Yadav 2009 [97]
5.4. Jia 2011 [70]
5.5. Opatz 2013 [16]
5.6. Yamaguchi 2014 [98]
6. Conclusions
Lead Author | Year | Lamellarin | Overall Yield | Linear Steps | Starting from |
---|---|---|---|---|---|
Steglich | 1997 | G trimethyl ether | 33% | 4 | 3-(3,4-Dimethoxyphenyl)pyruvic acid |
Banwell | 1997 | K | 58% | 7 | 4-Isopropoxy-3-methoxybenzaldehyde |
Iwao | 1997 | H | 4% | 10 | 3-Benzyloxy-4-methoxybenzaldehyde |
D | 5% | 10 | 3-Benzyloxy-4-methoxybenzaldehyde | ||
Steglich | 2000 | L | 18% | 9 | 3-Isopropoxy-4-methoxybenzaldeyde |
Guitián | 2001 | I | 4% | 9 | 3-Isopropoxy-4-methoxybenzaldeyde |
K | 6% | 9 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
Ruchirawat | 2001 | G trimethyl ether | 27% | 5 | 2‘-Hydroxy-4′,5′-dimethoxyacetophenone |
Faulkner | 2002 | H | 17% | 9 | 3-Isopropoxy-4-methoxybenzaldehyde |
α | 17% | 9 | 3-Isopropoxy-4-methoxybenzaldehyde | ||
α 13,20-disulfate | 14% | 10 | 3-Isopropoxy-4-methoxybenzaldehyde | ||
Iwao | 2003 | G trimethyl ether | 12% | 9 | Homoveratrylamine |
Handy | 2004 | G trimethyl ether | 10% | 8 | Ethyl 4-bromopyrrole-2-carboxylate |
Álvarez | 2005 | D | 3% | 16 | 3-Isopropoxy-4-methoxybenzaldehyde |
Iwao | 2006 | N | 16% | 12 | 3-Isopropoxy-4-methoxybenzaldeyde |
D | 18% | 12 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
L | 19% | 11 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
2006 | α 20-sulfate | 24% | 14 | Homoveratrylamine | |
Steglich | 2006 | K | 18% | 9 | 4-Bromo-2,3-dimethoxybenzaldehyde |
G | 27% | 7 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
Ruchirawat | 2006 | I, C, T, F, K, E, dihydro‑η, G trimethyl ether, J, U, L, G, χ, Y ξ, B, W, ε, M, X, η, J‑DB, α, N, G‑DB, D, Y‑DB | 5%–34% (saturated) 4%–30% (unsaturated) | 8–9 (saturated) 11–12 (unsaturated) | 3-Benzyloxy-4-methoxybenzaldehyde 4-Benzyloxy-3-methoxybenzaldehyde Veratraldehyde 2,3,4-Trimethoxybenzaldehyde 2,4-Dibenzyloxy-5-methoxybenzaldehyde 2,5-Dibenzyloxy-4-methoxybenzaldehyde 2-Benzyloxy-4,5-dimethoxybenzaldehyde |
Opatz | 2008 | U | 14% | 9 | 3-Benzyloxy-4-methoxybenzaldehyde |
G trimethyl ether | 18% | 8 | Veratraldehyde | ||
Yadav | 2009 | G trimethyl ether | 44% | 4 | Veratrole |
Iwao | 2010 | α 20-sulfate | 6% | 15 | 3-Isopropoxy-4-methoxybenzaldeyde |
α 13-sulfate | 4% | 15 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
α 13,20-disulfate | 9% | 14 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
Banwell | 2011 | G trimethyl ether | 3% | 10 | N-Boc-pyrrole |
S | 7% | 11 | 3,4-Diisopropoxybenzaldehyde | ||
Jia | 2011 | D | 13% | 9 | 4-Isopropoxy-3-methoxybenzaldehyde |
H | 13% | 9 | 4-Isopropoxy-3-methoxybenzaldehyde | ||
Banwell | 2012 | T | 41% | 6 | 3-Isopropoxy-4-methoxybenzaldeyde |
W | 42% | 7 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
U | 45% | 6 | 3-Isopropoxy-4-methoxybenzaldeyde | ||
Opatz | 2013 | η | 57% | 9 | 4-Benzyloxy-3-methoxyphenylacetonitrile |
dihydro-η | 62% | 8 | 4-Benzyloxy-3-methoxyphenylacetonitrile | ||
G trimethyl ether | 69% | 7 | 3,4-Dimethoxyphenylacetonitrile | ||
Iwao | 2014 | L | 30% | 13 | N-Boc-2,5-dibromopyrrole |
N | 42% | 11 | N-Boc-2,5-dibromopyrrole | ||
Yamaguchi | 2014 | C | 3% | 8 | 2,3,4-Trimethoxybenzaldehyde |
I | 3% | 8 | 2,3,4-Trimethoxybenzaldehyde |
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Imbri, D.; Tauber, J.; Opatz, T. Synthetic Approaches to the Lamellarins—A Comprehensive Review. Mar. Drugs 2014, 12, 6142-6177. https://doi.org/10.3390/md12126142
Imbri D, Tauber J, Opatz T. Synthetic Approaches to the Lamellarins—A Comprehensive Review. Marine Drugs. 2014; 12(12):6142-6177. https://doi.org/10.3390/md12126142
Chicago/Turabian StyleImbri, Dennis, Johannes Tauber, and Till Opatz. 2014. "Synthetic Approaches to the Lamellarins—A Comprehensive Review" Marine Drugs 12, no. 12: 6142-6177. https://doi.org/10.3390/md12126142