A synthesis of the ring system of terpestacin

Total Synthesis of (±)-Terpestacin and (±)-11-epi-Terpestacin

“…In 1998 Tatsuta also reported a synthesis of the racemate and by Heissler (1999) . In 2005 we disclosed a synthesis of the cyclopentenone core structure of terpestacin …”

A convergent stereocontrolled total synthesis of (−)-terpestacin

“…Consequently, terpestacin became an important target of total synthesis shortly after its discovery. So far, four total syntheses of (−)-terpestacin by Tatsuta and Masuda (1998), 7a Myers et al (2002), 6a Jamison and Chan (2003), 4a and more recently by Trost et al (2007), 8 and two for the racemate by Tatsuta et al (1998) 7b and Tius and Berger (2007), 9a respectively, have been reported, together with three approaches to the fused ring system independently described by Takeda et al (1995), 10 Heissler and co-workers (1999), 11 and Tius and Berger (2005), 9b respectively.…”

The McMurry Coupling and Related Reactions

“…Indeed, intramolecular carbonyl coupling has proved to be one of the best methods for cophytols 120 and 121 [158,159], and various hydroxy-and epoxy-cembrenes such as 122-124 [160][161][162][163]. Compounds 125 and 126 possess the ring systems of terpestacin and trinervitane, respectively [164,165]. The synthesis of compactin and mevinolin, 127 (R ¼ H, Me), could be performed in an efficient and reproducible way by using titanium-graphite in place of the standard TiCl 3 -Zn(Cu) combination [166].…”