Intramolecular cyclodehydration of (4S)-(+)-4-carboxyethyl-4-(pyrrol-1-yl)butanal as the key step in the formal synthesis of (S)-(−)-Myrmicarin 217

5,6-Dihydroindolizines as Convenient Precursors of Indolizidine 167B and Analogues

“…8 5,6-Dihydroindolizines are rare and we employed them in a formal synthesis of Myrmicarin 217. 9 We now show that these compounds can be used as precursors of indolizidine 167B and analogues.…”

Synthetic and Theoretical Investigations of Myrmicarin Biosynthesis

“…To date, a number of total syntheses of the simplest members (i.e. 1 – 3 ) have been achieved,2 some of which are enantioselective;2d–f however, none of the higher‐order members has been synthesized in the laboratory despite the existence of several reasonable biosynthetic hypotheses for how structures 4 – 6 might be formed in nature 1b. 3b In all cases, efforts to reduce these ideas to practice have led to materials that are stereo‐ and regioisomeric to the natural isolates.…”

Indoles and Indolizidines

“…Numerous members belong to this family of alkaloids, including M430A 159 , and simpler tricyclic compounds M215A 9 , M215B 10 , and M217 11 (Figure 7.4 ). Notable synthetic achievements in this area have been reviewed [116] , and include the racemic synthesis of M217 by Schr ö der and Francke [117] , the synthesis of ( + ) -M217 by Vall é e [118] , the formal synthesis of ( − ) -M217 by Lazzaroni [119] , as well as the syntheses of M215A and M215B by Vall é e [120] . Notable synthetic achievements in this area have been reviewed [116] , and include the racemic synthesis of M217 by Schr ö der and Francke [117] , the synthesis of ( + ) -M217 by Vall é e [118] , the formal synthesis of ( − ) -M217 by Lazzaroni [119] , as well as the syntheses of M215A and M215B by Vall é e [120] .…”