Table 2.
Synthesis of Lamellarins and Related Pyrrole-Derived Alkaloids
| lamellarin and related alkaloids | research group | synthesis strategy | ref |
|---|---|---|---|
| lamellarins D, H (35, 37) | Iwao, Ishibashi | N-ylide-mediated pyrrole formation | 31 |
| lamellarin D (35) | Albericio, Álvarez | sequential and regioselective bromination/Suzuki cross-coupling procedure | 32 |
| lamellarin D analogues | Albericio, Álvarez | sequential and regioselective bromination/palladium-catalyzed Suzuki cross-coupling procedure | 33 |
| lamellarins D, L, N (35, 15, 40) | Iwao, Ishibashi | Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki–Miyaura coupling reactions | 34 |
| lamellarin H (37) and its derivatives | You | intermediate for lamellarin | 35 |
| lamellarins I, K (10, 12) | Guitián | intramolecular [3 + 2] cycloadditon pathway | 36 |
| lamellarins G, K, lukianol A, ningalin B (8, 12, 56, 74) | Steglich | biomimetic synthesis | 37 |
| lamellarin G trimethyl ether | Steglich | biomimetic synthesis | 38 |
| lamellarin G trimethyl ether | Ruchirawat | N-ylide-mediated pyrrole formation | 39 |
| lamellarin G trimethyl ether, permethyl storniamide A, ningalin B (74) | Iwao, Ishibashi | Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki–Miyaura coupling reactions | 40 |
| lamellarin G trimethyl ether | Handy | three iterative halogenation/cross-coupling reactions | 41 |
| lamellarin K (12) | Banwell | intramolecular [3 + 2] cycloadditon pathway | 42 |
| lamellarins K, L (12,15) | Ruchirawat | convergent synthetic approach; Michael addition/ring-closure reaction | 43 |
| lamellarin L (15) | Steglich | biomimetic total synthesis | 44 |
| lamellarins U, L (22,15) | Albericio, Álvarez | solid-phase total synthesis; Baeyer–Villiger reaction and an intramolucular [3 + 2] cycloaddition | 45 |
| lamellarins U, L, O, Q (22, 15, 52, 54) | Albericio, Álvarez | solid-phase total synthesis; intramolucular [3 + 2] cycloaddition, two successive and selective cross-coupling reactions | 46 |
| lamellarins O, Q, lukianol A (52, 54, 56) | Banwell | convergent synthesis; Stille, Suzuki, or Negishi cross-coupling reactions | 47 |
| lamellarins Q, O (54,52) | Albericio, Álvarez | solid-phase synthesis; Negishi/Suzuki cross-coupling reactions | 48 |
| lamellarin T hybrids | Banwell | Negishi cross-coupling reaction | 49 |
| lamellarin α, lamellarin α 13,20-disulfate, lamellarin H (45,47,37) | Faulkner | intramolecular [3 + 2] cycloaddition pathway | 50 |
| lamellarin α 20-sulfate (46) | Iwao, Ishibashi | Hinsberg-type pyrrole synthesis and Suzuki–Miyaura coupling reaction | 51 |
| lamellarins C, E–G, I–L, T, U, Y, χ (3, 6–8, 10–12, 15, 19, 22, 26, 31) | Ruchirawat | Michael addition/ring-closure reaction | 52 |
| lukianol A (56), lamellarin O dimethyl ether | Fürstner | titanium-mediated formation | 53 |
| lukianol A (56), lamellarin O dimethyl ether | Gupton | vinylogous iminium chemisty | 54 |
| lukianol A (56) | Wong | palladium-catalyzed Sonogashira, Heck, and Suzuki cross-coupling reactions | 55 |
| lukianol A (56) | Steglish | biomimetic synthesis | 56 |
| polycitrin A (60) | Steglish | biomimetic total synthesis | 57 |
| polycitrin A (60), prepolycitrin A (62) | Correia | palladium-catalyzed Heck diarylation | 58 |
| polycitrin A (60) | Steglich | biomimetic synthesis | 59 |
| polycitrin B (61) | Beccalli | palladium-catalyzed cross-coupling reaction | 60 |
| polycitones A, B (58, 59) | Steglich | total synthesis; Friedel–Crafts reaction | 61 |
| polycitones A, B (58, 59) | Gupton | vinylogous iminium chemisty | 62 |
| storniamide A nonamethyl ether | Steglich | biomimetic synthesis | 63 |
| permethyl storniamide A | Fürstner | palladium-catalyzed Suzuki and Negishi cross-coupling reactions | 64 |
| didemnimide A (67) | Berlinck, Piers, Andersen | biomimetic synthesis | 21 |
| didemnimides A, B (67, 68) | Cava | K+t-BuO−-catalyzed condensation | 65 |
| didemnimide C (69) | Steglich | Stille coupling reaction | 66 |
| didemnimide C (69) | Piers | biomimetic synthesis | 67 |
| ningalin A (73), lamellarin O (52), lukianol A (56), permethyl storniamide A | Boger | Diels–Alder reaction/ring contraction pathway | 68 |
| ningalin B (74) | Boger | heterocyclic azadiene Diels–Alder reaction | 69 |
| ningalin B (74) and its analogs | Boger | heterocyclic azadiene Diels–Alder strategy | 70 |
| ningalin B (74) | Bullington | regioselective synthesis | 71 |
| ningalin B hexamethyl ether | Gupton | vinylogous iminium chemistry | 72 |
| ningalin C, purpurone (75,77) | Steglich | biomimetic total synthesis | 73 |
| ningalin C (75) | Ruchirawat | one-pot reaction | 74 |
| ningalin D (76) | Boger | Heterocyclic azadiene Diels–Alder reaction | 75 |