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.
Highlights
The Lamellarins were first isolated by Faulkner and co-workers in 1985 from the prosobranch mollusc Lamellaria sp. [1,2,3,4,5,6,7,8,9,10,11] and represent a group of more than 50 polycyclic marine alkaloids which contain a central pyrrole moiety
The syntheses are grouped by the class of the lamellarin synthesized as well as by the strategy used for the construction and/or decoration of the central pyrrole ring
N-deprotection with Bu4NF, pyrrole 30 was obtained which was further deprotected with BCl3 (Iwao had demonstrated already in his synthesis of 2005 that BCl3 is a selective reagent for the cleavage of benzyl or isopropyl ethers in lamellarin precursors without affecting methyl ethers, which on the other hand are removed by BBr3—vide infra) to afford lamellarin Q (10) in 7% over seven steps
Summary
The Lamellarins were first isolated by Faulkner and co-workers in 1985 from the prosobranch mollusc Lamellaria sp. [1,2,3,4,5,6,7,8,9,10,11] and represent a group of more than 50 polycyclic marine alkaloids which contain a central pyrrole moiety. Structurally simpler representatives of the lamellarins containing a 3,4-diaryl substituted pyrrole core (type II) are known (Figure 1) [4,5]. Their substitution in terms of a varying oxygenation and O-substitution pattern provides the basis for their structural diversity as well as for notable differences in their biological activity. Structure activity relationships were investigated with a particular emphasis on lamellarin D, the most cytotoxic representative of the lamellarins [24,25,26,27,28] These studies resulted in a pharmacophore model explaining the structural features required for inhibiting the action of eukaryotic topoisomerase I, an enzyme required for transcription and replication of DNA [29,30,31,32,33,34,35,36]. The syntheses are grouped by the class of the lamellarin synthesized (type II vs. type Ia/Ib) as well as by the strategy used for the construction and/or decoration of the central pyrrole ring
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