𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Revision of the configuration at C-7 of salutaridinol-I, the natural intermidiate in morphine biosynthesis

✍ Scribed by Hermann Lotter; Jürgen Gollwitzer; Meinhart H. Zenk

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
289 KB
Volume
33
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The biologically active reduction product of salutaridine. which was generated by synthesis and by a highly subs&ate specific enzyme fronr@upmr somnijivwn, was shown by X-ray crystallography lo have the opposite configuration at C-7 as hitherto assumed. ?he (7S)-con@red biologically active alkaloid will be called in future salukuidinol. its inactive epime& 7-epi-salutaridinol.

Barton and Cohen1 have on theoretical grounds proposed that the crucial Cl2 -Cl3 bond of morphine alkaloids can be envisaged as being formed by intramolecular phenolic coupling of (R )-mticulme. In a series of brilhant experiments.2 experimental proof has been obtained that (R )-reticuliie is transformed to the dienone, salutaridine. by regioselectlve pun?-onho oxidative coupling. Chemically synthesized salutaridine is transformed in vivo into thebaine, codeine, and morphine in the Pup&r somniferum plant The biocatalysts involved in this

📜 SIMILAR VOLUMES

Absolute configuration of the substituen
Absolute configuration of the substituent at C-7 in guaiol
✍ Hitoshi Minato 📂 Article 📅 1961 🏛 Elsevier Science 🌐 French ⚖ 214 KB

Osaka, Japan IN the preceding papers,' it was eetabliehed that both the C-4 and the C-10 methyl Bronps in guaiol (I) poeseas the a-configuration. Now the question remains as to whether the eubetituent at C-7 in guaiol is aor $-oriented. In thin rxperiment, an attempt was made to determine the absolu