Concepedia

Formal Total Synthesis of (—)‐Morphine by Cuprate Conjugate Addition

Johann Mulzer, Gerd Dürner, Dirk Trauner

Angewandte Chemie International Edition in English · 1996 · 58 citations · 16 references

DOI

Concepts

Abstract

Conjugate addition of a vinyl cuprate to the sterically and electronically very demanding enone 1 is the key step of a short asymmetric total synthesis of (—)-dihydro-codeinone (2), an immediate precursor of (-)-morphine.

References

16

The reactions of combined organocuprate-chlorotrimethylsilane reagents with conjugated carbonyl compounds

E. J. Corey, Neil W. Boaz · Tetrahedron Letters · 1985 · 256 citations

, , +5

1,1′-(azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for mitsunobu reaction

Tetsuto Tsunoda, Yoshiko Yamamiya, Shô Itô · Tetrahedron Letters · 1993 · 220 citations

, , +3

Chlorosilane-accelerated conjugate addition of catalytic and stoichiometric organocopper reagents

Satoshi Matsuzawa, Yoshiaki Horiguchi, Eiichi Nakamura et al. · Tetrahedron · 1989 · 195 citations

, , +10

Asymmetric synthesis of either enantiomer of opium alkaloids and morphinans. Total synthesis of (-)- and (+)-dihydrocodeinone and (-)- and (+)-morphine

Chang Yong Hong, Noriyuki Kado, Larry E. Overman · Journal of the American Chemical Society · 1993 · 194 citations

, , +10

Synthetic opium alkaloids and derivatives. A short total synthesis of (.+-.)-dihydrothebainone, (.+-.)-dihydrocodeinone, and (.+-.)-nordihydrocodeinone as an approach to a practical synthesis of morphine, codeine, and congeners

Kenner C. Rice · The Journal of Organic Chemistry · 1980 · 122 citations

, , +5