The structure of clavicipitic acid, an azepinoindole derivative from Claviceps fusiformis

ChemInform Abstract: Strategies for the Total Synthesis of Clavicipitic Acid

“…[2] They further provedt hat clavicipitic acid exists as two diastereomers (cis-isomer 2a and trans-isomer 2b). [3] Clavicipitic acid is considered as ad erailmentp roduct of ergot alkaloid biosynthesis. [4] Its biosynthetic pathway starts from prenylation of tryptophan by dimethylallyl pyrophosphate (DMAPP) (3), which furnishes 4-dimethylallyltryptophan( DMAT) (4).…”

“…[3] Clavicipitic acid is considered as ad erailmentp roduct of ergot alkaloid biosynthesis. [4] Its biosynthetic pathway starts from prenylation of tryptophan by dimethylallyl pyrophosphate (DMAPP) (3), which furnishes 4-dimethylallyltryptophan( DMAT) (4). DMATi s convertedt oo ther ergot alkaloids in normalb iosynthesis.…”

Short syntheses of the tricyclic indole alkaloids cimitrypazepine and fargesine

“…Introduction Naturally occurring azepino [5,4,3-cd]indoles have been isolated from diverse natural sources ( Figure 1). This group of alkaloids include aurantioclavine (as a mixture of diastereomers) isolated from the fungus Penicillium aurantiovirens, 1 clavicipitic acid from the fungus Claviceps fusiformis, 2 the diastereomeric alkaloids hyrtireticuline C and D from the marine sponge Hyrtios reticulatus, 3 and fargesine from the roots and stems of Evodia fargesii. 4 In addition, cimitrypazepine was identified in the roots and rhizomes of black cohosh (Cimicifuga racemosa).…”

Hyrtinadines C and D, New Azepinoindole-Type Alkaloids from a Marine Sponge <i>Hyrtios</i> sp.

“…Though the number of natural products possessing a 3,4-fused azepinoindole skeleton was limited, 6,8,[10][11][12][13][14][15][16][17][18] those compounds were attracting great interest as synthetic targets. 19) Therefore, 1 and 2 were the new members of relatively rare class of natural products.…”