Total synthesis of two naturally occurring polyacetylenic glucosides (−)-bidensyneoside A1 and B, and an analogue of (−)-bidensyneoside C

Polyacetylene Glycosides: Isolation, Biological Activities and Synthesis

“…The same group described the synthesis of bidensyneoside A 1 and B. [178] The strategy was again based on the Cadiot-Chodkiewicz coupling reaction for the formation of spÀ sp bond using the bromoalkyne as a common precursor for both natural products. The authors attributed the lower yield for bidensyneoside B to a partial decomposition of triyne 87 during the purification process.…”

Total synthesis of polyyne natural products

“…2) have been shown to inhibit histamine release in rat mast cells and the production of nitric oxide. Their interesting biological activities and chemical structures have started to attract attentions in their synthetic studies [18,19,51].…”

“…Attracted by the diverse biological activities [10e15] and the challenges of introducing stereocenters into reactive compounds, we commenced our first synthesis of a naturally occurring acetylenic alcohol, (S,S)-and (R,R)-adociacetylene B (1), in 2001 [16]. After the inaugural synthesis of adociacetylene B (1), graduate student Hamilton Dickson took on the tetrayne target, minquartynoic acid [17], and Ryan Fox, an undergraduate at the time, took on the polyyne glycosides, bidensyneosides [18,19]. This account describes the syntheses of these two groups of polyyne natural products first followed by the synthesis of C 2 symmetric acetylenic compounds.…”

A Short Synthesis of (S)‐(+)‐Siphonodiol.

“…After 1h, TLC indicated that the starting material had all disappeared. The reaction was diluted with 100 ml of ether and washed twice with saturated NH 4 Cl solution. The aqueous layer was extracted with ether and the combined organic layers were washed with brine, dried over MgSO 4 , and the solvent was removed under reduced pressure.…”