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Review
. 2014 Dec 18;12(12):6142-77.
doi: 10.3390/md12126142.

Synthetic approaches to the lamellarins--a comprehensive review

Dennis Imbri  1 , Johannes Tauber  2 , Till Opatz  3
Affiliations
Review

Synthetic approaches to the lamellarins--a comprehensive review

Dennis Imbri et al. Mar Drugs. .

Abstract

The present review discusses the known synthetic routes to the lamellarin alkaloids published until 2014. It begins with syntheses of the structurally simpler type-II lamellarins and then focuses on the larger class of the 5,6-saturated and -unsaturated type-I lamellarins. The syntheses are grouped by the strategy employed for the assembly of the central pyrrole ring.

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Figures

Figure 1
Figure 1
Structure of lamellarins type Ia, Ib and II [16].
Scheme 1
Scheme 1
Synthesis of lamellarin O dimethyl ether by Fürstner et al. [65].
Scheme 2
Scheme 2
Synthesis of lamellarins O and Q by Banwell et al. [66].
Scheme 3
Scheme 3
Synthesis of lamellarin O by Boger et al. [67].
Scheme 4
Scheme 4
Synthesis of lamellarins O and Q by Álvarez et al. [68].
Scheme 5
Scheme 5
Synthesis of lamellarins O, P, Q and R by Iwao et al. [69].
Scheme 6
Scheme 6
Synthesis of lamellarin R by Jia et al. [70].
Scheme 7
Scheme 7
Synthesis of lamellarins O and Q by Vazquez et al. [71].
Scheme 8
Scheme 8
Synthesis of lamellarin G trimethyl ether by Iwao et al. [72].
Scheme 9
Scheme 9
Synthesis of lamellarins D, N and L by Iwao et al. [73].
Scheme 10
Scheme 10
Synthesis of lamellarin α 20-sulfate by Iwao et al. [74].
Scheme 11
Scheme 11
Synthesis of lamellarins α 13-sulfate, α 20-sulfate and α 13,20-disulfate by Iwao et al. [75].
Scheme 12
Scheme 12
Synthesis of lamellarin G trimethyl ether by Handy et al. [78].
Scheme 13
Scheme 13
Synthesis of lamellarin D by Álvarez et al. [79].
Scheme 14
Scheme 14
Synthesis of lamellarin G trimethyl ether and lamellarin S by Banwell et al. [80].
Scheme 15
Scheme 15
Synthesis of lamellarins N and L by Iwao et al. [81].
Scheme 16
Scheme 16
Synthesis of lamellarins D and H by Iwao et al. [82].
Scheme 17
Scheme 17
Synthesis of lamellarins I and K by Guitián et al. [83].
Scheme 18
Scheme 18
Synthesis of lamellarin G trimethyl ether by Ruchirawat et al. [84].
Scheme 19
Scheme 19
Synthesis of natural and non-natural occurring lamellarins by Ruchirawat et al. [86].
Scheme 20
Scheme 20
Synthesis of lamellarin G trimethyl ether and lamellarin U by Opatz et al. [87].
Scheme 21
Scheme 21
Synthesis of lamellarin K by Banwell et al. [88].
Scheme 22
Scheme 22
Synthesis of lamellarins H, α and α 13,20-disulfate by Faulkner et al. [89].
Scheme 23
Scheme 23
Solid-Phase-Synthesis of lamellarin U by Álvarez et al. [90].
Scheme 24
Scheme 24
Synthesis of lamellarin G trimethyl ether by Steglich et al. [92].
Scheme 25
Scheme 25
Synthesis of lamellarin L by Steglich et al. [77].
Scheme 26
Scheme 26
Synthesis of lamellarins G and K by Steglich et al. [93].
Scheme 27
Scheme 27
Synthesis of common intermediate 158 by Gupton et al. [94].
Scheme 28
Scheme 28
Synthesis of lamellarin G trimethyl ether by Yadav et al. [97].
Scheme 29
Scheme 29
Synthesis of lamellarins D and H by Jia et al. [70].
Scheme 30
Scheme 30
Synthesis of lamellarin G trimethyl ether, dihydrolamellarin η and lamellarin η by Opatz et al. [16].
Scheme 31
Scheme 31
Synthesis of lamellarins C and I by Yamaguchi et al. [98].
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References

    1. Andersen R.J., Faulkner D.J., He C.H., Van Duyne G.D., Clardy J. Metabolites of the marine prosobranch mollusk Lamellaria sp. J. Am. Chem. Soc. 1985;107:5492–5495. doi: 10.1021/ja00305a027. - DOI
    1. Lindquist N., Fenical W., van Duyne G.D., Clardy J. New alkaloids of the lamellarin class from the marine ascidian Didemnum chartaceum. J. Org. Chem. 1988;53:4570–4574. doi: 10.1021/jo00254a029. - DOI
    1. Carroll A.R., Bowden B.F., Coll J.C. Studies of Australian ascidians. I. Six new lamellarin-class alkaloids from a colonial ascidian, Didemnum sp. Aust. J. Chem. 1993;46:489–501. doi: 10.1071/CH9930489. - DOI
    1. Urban S., Butler M.S., Capon R.J. Lamellarins O and P: New aromatic metabolites from the Australian marine sponge Dendrilla cactos. Aust. J. Chem. 1994;47:1919–1924. doi: 10.1071/CH9941919. - DOI
    1. Urban S., Hobbs L., Hooper J.N.A., Capon R.J. Lamellarins Q and R: New aromatic metabolites from an Australian marine sponge, Dendrilla cactos. Aust. J. Chem. 1995;48:1491–1494. doi: 10.1071/CH9951491. - DOI

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