Total synthesis of (.+-.)-3-deoxy-7,8-dihydromorphinone

Abstract

of pure N-nucleoside 9 was isolated after flash chromatography. The reaction likewise proceeded similarly with 0.25 mmol of red HgO as the catalyst.Acknowledgment. We thank Drs. John S. Driscoll and James A. Kelley of this laboratory for their many helpful discussions during the course of this work.

Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**

“…However, boron plays a non‐innocent role in these processes and photochemical net‐reductive transformations of these substrates remains limited. Reductive defunctionalization is a powerful synthetic tactic to leverage aniline and phenol activating groups in a traceless manner [59–62] . Current methods to remove these directing groups rely on harsh dissolving metal conditions [63, 64] or palladium catalysis [65, 66] .…”

“…Reductive defunctionalization is ap owerful synthetic tactic to leverage aniline and phenol activating groups in at raceless manner. [59][60][61][62] Current methods to remove these directing groups rely on harsh dissolving metal conditions [63,64] or palladium catalysis. [65,66] We envisioned that cleavage of these strong bonds was ap erfect arena to explore new potent reductants given recently reported halogen-atom transfer strategies,w hich in some cases can circumvent deeply reducing potentials, [67] are unlikely to be amenable to the cleavage of these less polarizable heteroatoms.…”

Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**

“…Reductive defunctionalization is ap owerful synthetic tactic to leverage aniline and phenol activating groups in at raceless manner. [59][60][61][62] Current methods to remove these directing groups rely on harsh dissolving metal conditions [63,64] or palladium catalysis. [65,66] We envisioned that cleavage of these strong bonds was ap erfect arena to explore new potent reductants given recently reported halogen-atom transfer strategies,w hich in some cases can circumvent deeply reducing potentials, [67] are unlikely to be amenable to the cleavage of these less polarizable heteroatoms.…”

Recent developments in the Birch reduction of aromatic compounds: applications to the synthesis of natural products

“…The general methodology has been applied to the synthesis of oplopanone (40),h0 pregn-4-en-20-one (43),h (Z)-henicos-6-en-11-one (48) [which is the male sex attractant of the Douglas Fir Tussock Moth (Orgyiu pseud~tsugata)],~~ and the alkaloid secodaphniphylline (53),58 respectively (Schemes 9, 10, 1 1, and…”