Table 1.
Comparison of completed total syntheses of the type-I lamellarins.
| 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 |