Isoquinoline Alkaloids Research 1972–1977 by Maurice Shamma

By Maurice Shamma

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53 The biogenesis of cryptopleurospermine probably involves oxidation of a tetrahydrobenzylisoquinoline precursor to an a-ketoimmonium salt which, upon conversion to its pseudobase and further N-alkylation, undergoes cleavage of ring B. 0 Hz) (J2' •• OCH 3 1. NaBH. 88 (s) 2. HlO. 6. , dopa may be metabolized in at least two ways to yield dopamine and 3,4-dihydroxyphenylpyruvic acid. Decarboxylation of dopa to yield dopamine is actually favored over transamination to the substituted pyruvic acid.

Nelumbo nuci/era Gaertn. 4 and Aconitum japonicum Decne. 2. 1. The Use of Reissert Compounds 12 A new synthesis of petaline proceeds through a Reissert derivative of 7-methoxy-8-hydroxyisoquinoline,13 as shown below. (In p-methoxybenzoyl chloride, CH30~~N KCN CHaO I. NaH, DMF 2. -rC O~ # ben~1 chlonde >3. , OHe II OH OH D/OCH3 ( I. CH31 2. NaBH. 3. -" ) CHaO ~ I OH OH e /CH 3 N Ie "CH3 '~ ~OCHa OCH3 Petaline The condensation of aromatic aldehydes with the anion of an N-benzoyl Reissert compound is known to proceed through an intramolecular rearrangement to give esters of type 1.

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