Synthesis of Polyacetylenic Acids Isolated from Heisteria acuminata

Abstract

Four linear polyacetylenic compounds were synthesized. Pentadeca-6,8,10-triynoic acid 1 and octadeca-8,10,12-triynoic acid 2 were synthesized by using acetylene coupling reactions. The syntheses of (Z)-hexadec-11-en-7,9-diynoic acid 3 and (Z)-octadec-12-en-7,9-diynoic acid 4 by using vinylic telluride coupling reactions were accomplished.

Gold Chloride (AuCl<sub>3</sub>) Catalyzed Expeditious Homocoupling of Terminal Alkynes at Ambient and Solvent Free Conditions: Impact of Sodium Acetate on the Reaction Yield

“…From the above results, it is evident that organic bases have a promoting effect not only on the yield but also on the reaction time of terminal alkyne homocoupling. 1-3, 5, 7, 8), but better yields were obtained in acetonitrile, 1, 4-dioxane, and THF, where acetonitrile was found to be the most suitable solvent yielding 92% desired product(table 2, entries 4,6,10). When the reaction was put under solvent free conditions, the product yield increased to >95% within 30 min (table 2, entry 1).…”

“…Diyne compounds have received significant attention because of their applications not only in material chemistry but also in the formation of valuable intermediates for natural products [2] and pharmaceuticals such as antitumor [3], anti-inflammatory [4] and antifungal agents [5]. As the emerging importance much interest has been paid for the development of new and efficient methods for the synthesis of diynes [6].…”

Synthesis of 1,3-diynes via detelluration of bis(ethynyl)tellurides

“…2,3 Compounds containing chains of conjugated triple bonds 4,5 are of paramount importance as versatile and useful building blocks in organic synthesis. Among these compounds, 1,3-butadiynes 6 have been prominently utilized as substructures in the formation of valuable intermediates for natural products 7 and pharmaceuticals such as antitumor, 8 antibacterial, 9 anti-inflammatory, 10 and antifungal agents. 11 These conjugated diynes also serve as the core functional group in organic molecular materials such as linearly σ-conjugated acetylenic oligomers and polymers, 12 macrocycles 13 (Figure 1), and supramolecular scaffolds.…”

Copper‐Catalyzed Cross‐Coupling of Thiols with 1‐Iodo‐2‐chalcogenoalkenes

“…This makes the double bond in vinylic chalcogenides responsive towards both nucleophilic and electrophilic attack, an extremely useful feature in organic synthesis. [2] The scope and application of organosulfur chemistry has increased tremendously because sulfur-containing groups serve as an important auxiliary function in synthetic sequences. Most of the synthetic transformations that use organosulfur compounds have involved the use of vinylic sulfides.…”