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Direct and Sequential Removal of Phenolic Oxygen Functions in S-(+)-Bulbocapnine, S-(+)-Boldine and R-(-)-Apomorphine

Year: 1977

Type: article

Abstract: Three poly-oxygenated aporphines have been transformed into a variety of desoxy congeners.This was readily accomplished by O-dealkylation with BBr3 and BC13 to cleave methoxyl and methylenedioxy groups, respectively, followed by reductive elimination of the resulting phenols as their tetrazoyl ethers or diethyl phosphate esters.The simultaneous elimination of two o-positioned hydroxy groups by these procedures was difficult to accomplish without racemization.

Source: Heterocycles

DOI: 10.3987/s-1977-01-0277

Authors: Arnold Brossi, Mohamad F. Rahman, Kenner C. Rice, Max Gerecke, René Borer, Jay P. O’Brien, Sidney Teitel

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

OpenAlex ID: W2057366308

FWCI: 0.617

Cites: 1

Cited by: 5

Related to: 10