Synthesis of Macrocyclic Compounds by Ring Closing Metathesis

Abstract

Synthesis of macrocyclic compounds including natural products with varying complexities by ring closing metathesis is described. Twelve to very large rings that have been synthesized in moderate to good yields and the synthesis of larger rings as a part of bi-or poly-cyclic systems are also described in this review. The effectiveness of the Grubbs' catalyst towards the RCM in presence of free alcohols, epoxides as well as with various silyl ethers is also presented. In addition to these, the application of RCM towards the syntheses of various naturally occurring macrolides, lactams and unnatural cyclic poly ethers, catenanes etc. are described.

Unusually stable tungstenacyclobutadienes featuring an ONO trianionic pincer-type ligand

“…Transition metal-catalyzed alkyne cross metathesis (ACM), [1][2][3][4][5][6][7][8][9][10][11][12] nitrile-alkyne cross metathesis (NACM), 1,[13][14][15][16][17][18][19][20] ring-closing alkyne metathesis (RCAM), [21][22][23][24] ring-opening alkyne metathesis polymerization (ROAMP), [25][26][27][28] and acyclic diyne metathesis (ADIMET) [29][30][31] continue to attract considerable interest as useful catalytic methods for creating CuC triple bonds. Work still remains to create highly active catalysts that tolerate a broad scope of substrates comparable to their alkene metathesis counterparts.…”

Entropy-driven ring-opening olefin metathesis polymerizations of macrocycles

“…As a result of the broad reach of modern ring-closing olefin metathesis, nearly any chemical moiety imaginable can be incorporated within a macrocycle [12][13][14] and from there be transferred into the main-chain of a polymer via subsequent ED-ROMP. Main-chain functionality that may be introduced by ED-ROMP includes, but is not limited to: sites…”

Highly Active Ruthenium Metathesis Catalysts Exhibiting Unprecedented Activity and Z-Selectivity

“…Many of these compounds contain a macrocyclic backbone either featuring a Z -olefin, or bearing functionality stereospecifically installed using a Z- olefin. 5,6,19,21 In fact, 18 and 19 are both currently in demand by the perfume industry (marketed as ambrettolide and civetone, respectively). 21 …”