Simple indole alkaloids and those with a non-rearranged monoterpenoid unit

Abstract

Covering: 2010-2011. Previous review: Nat. Prod. Rep. 2010, 27, 1630-1680This review covers the literature on simple indole alkaloids and those with a non-rearranged monoterpenoid unit from the beginning of 2010 up to the end of 2011, which includes newly isolated alkaloids, structure determinations, total syntheses and biological activities.

Applications of Bartoli indole synthesis

“…In fact, indolization was observed starting from nitrosoarenes (5). 51 Moreover, the elimination of an enolate molecule (3) has to lead ultimately to an aldehyde or a ketone (4). Actually, in our experiments, the aldehyde was detected among the reaction products, but in very low amounts, when water-soluble and volatile.…”

“…Bicyclic aromatic heterocycles containing nitrogen atoms, such as quinolines, isoquinolines, and indoles are present in all classes of organic compounds in the biological and medicinal arena. [3][4][5][6][7][8][9][10][11] In particular, over ten thousand biologically active indole derivatives have been identified to date. Of those, over 200 are currently marked as drugs or undergoing clinical trials.…”

Microindolinone A, a Novel 4,5,6,7-Tetrahydroindole, from the Deep-Sea-Derived Actinomycete <em>Microbacterium </em>sp. MCCC 1A11207

“…Noteworthily, for the first time, the absolute configuration of such saturated indole was determined. By comparing the 1 H-, 13 C-NMR, MS, and OR data with those reported in the literature, 18 known compounds were identified as pyrrole-2-carboxylic acid (2) (12) [27], 5-methyluracil (13) [26], dibutyl phthalate (14) [28], 4-hydroxyphenylacetic acid (15) [29], [32], and (5-hydroxymethyl-furan-2-yl)-methanol (19) [33]. Surprisingly, these 19 compounds were all firstly isolated from Microbacterium species.…”

“…Therefore, the absolute configuration of 1 was determined as 5R-hydroxy-4,5,6,7-tetrahydroindole-4-one, and named microindolinone A. Surprisingly, although indoles occur broadly in nature [13][14][15], the saturated ones were seldom discovered. As a matter of fact, the only one reported was 6,7-dihydroxy-4,5,6,7-tetrahydroindole-4-one from Nocardia sp., a soil-derived actinomycete [16].…”

A Photoinduced Cyclization Cascade—Total Synthesis of (−)‐Leuconoxine

“…[1] Among them, the leuconolam-leuconoxine-mersicarpine alkaloid family has been isolated from several Apocynaceae species. [2][3][4] It has immediately drawn significant attention from the synthetic community, which is reflected by four completed total syntheses in the last two years.…”