Total synthesis of (.+-.)-dimethyl secologanoside O-methyl ether

Synthesis of Iridoid Monoterpenes and Prostaglandins, via Photochemical Rearrangement of Bicyclo[2.2.1]hept‐5‐en‐2‐One

“…The 1 H and 13 C NMR spec tra of 5 were iden ti cal with those of an au then tic sam ple pre vi ously pro duced in our lab o ra tory. 11 Since com pound 5 had been already trans formed to loganin (8) and hydroxyloganin ( 9), this work con sti tutes a for mal to tal syn the sis of loganin (8) and hydroxyloganin (9) Treat ment of 4 with Jones re agent fol lowed by esterifica tion of the re sult ing acid with dia zo me thane fur nished keto es ter 6. The 1 H and 13 C NMR spec tra of 6 were iden ti cal with those of an au then tic sam ple pre vi ously pro duced in our lab o ra tory.…”

“…The readily avail able bicyclo[2.2.1]heptenone 1 was cho sen as the start ing ma te rial. 9 Ir ra di a tion of 1 in cyc lo hex -ane in Rayonet re ac tor ( 300 nm) af forded the 1,3-acyl shift prod uct bicyclo[3.2.0]heptenone 2 in 78% yield. Sub sequent ring en large ment of 2 with dia zo me thane gave a mixture of cyclopentanone 3 and regioisomer 4 in 1.5:1 ra tio.…”

Vitamin D: Enantioselective Synthesis of (3aR,4R,7aS)-4-Hydroxy-7a-methylperhydro-1-indenone, a Suitable CD-Ring Fragment

“…Several methods for the formation of 17 from 16 were explored, and the most practical was epoxidation of the TMS-enolether of 16 followed by acid-catalyzed hydrolysis. [21] The yield of pure 17 from 16 was 94%.…”

Studies towards the synthesis of secoiridoids

“…[7] The same strategy was also used by Liao [8] to synthesize (+/-)-forsythide. Chang [9] synthesized secologanoside aglycone and Trost [10] prepared loganine aglycone, respectively.…”