Lyngbyaloside, a Novel 2,3,4-Tri-O-methyl-6-deoxy-α-mannopyranoside Macrolide from Lyngbya bouillonii (Cyanobacteria)

Abstract

A novel 16-membered macrolide linked to a 2,3,4-tri-O-methyl-6-deoxy-α-mannopyranoside, lyngbyaloside (1), has been isolated from the blue-green alga Lyngbya bouillonii, collected on Laing Island (Papua New Guinea). Its structure has been established by a detailed high-field 2D NMR study. The relative configuration of 8 out of the 13 stereogenic carbon atoms is proposed from the analysis of NOE difference experiments.

Antineoplastic Agents. 510. Isolation and Structure of Dolastatin 19 from the Gulf of California Sea Hare Dolabella auricularia

“…16 On the basis of the H-H coupling constants J 14,15 (15 Hz) and J 16,17 (14 Hz), the configuration of the carbon-carbon double bonds in the diene was assigned as E geometry. Therefore, all of the relative stereochemistry on the 14-membered macrolide ring was assigned as 2S*, 3S*, 5R*, 6S*, 7R*, 9S*, 13S*, E 10,11 , E 14, 15 , and E 16,17 .…”

“…Furthermore, lyngbyaloside, a 16-membered macrolide similar to dolastatin 19, has been isolated from the blue-green alga Lyngbya bouillonii. 17 Other 14-membered macrolides similar to dolastatin 19, such as lyngbouilloside 18 and lyngbyaloside B, 19 have also been isolated from cyanobacteria.…”

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

“…Tri-O- (210)(211)(212)(213)(214)(215)(216)(217). The brominated glycosidic macrolide lyngbyaloside 160a is produced by the marine cyanobacterium Lyngbya bouillonii (218).…”

1,5-Hydride transfer protocol for the synthesis of β-branched polyketide structural units

“…The substitution pattern observed in 6 is of significant utility that it can be found in the skeleton of numerous b-branched polyketides, including neopeltolide 3 and lyngbyaloside. 4 Therefore, a new avenue to the formation of tertiary stereocenters and b-branched motifs such as 6 utilizing the hydride transfer would be useful for the synthesis of such natural products.…”