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DOI: 10.1055/s-2004-816009
Stereoselective Synthesis of Aporphine Alkaloids Using a Hypervalent Iodine(III) Reagent-Promoted Oxidative Nonphenolic Biaryl Coupling Reaction. Total Synthesis of (S)-(+)-Glaucine
Publication History
Publication Date:
15 March 2004 (online)
Abstract
The aporphine alkaloid (+)-glaucine (8a) and two other analogues 8b,c have been synthesized in good yield and high ee from the appropriate 1,2-diarylethylamine derivatives, which were in turn prepared using (S)-(+)-phenylglycinol as chiral support. Next, a sequence of simple transformations: N-alkylation with bromoacetaldehyde diethyl acetal, N-methylation, Pommeranz-Fritsch cyclization, and ionic hydrogenation led to the key intermediate, optically active, 1-benzyltetrahydroisoquinolines 7a-c. The final C-ring closure step was performed by C-C biaryl bond formation by an hypervalent iodine(III) reagent promoted oxidative coupling, affording the target heterocycles 8a-c in good yields and with no racemization at the formerly created stereogenic center.
Key words
alkaloids - amino alcohols - asymmetric synthesis - chiral auxiliaries - iodine
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