A review.The antitumor antibiotics belonging to the tetrahydroisoquinoline family have been studied thoroughly over the past 25 yr starting with the isolation of naphthylridinomycin in 1974.The two core structures of this family are the quinone and the aromatic core.To date, 55 natural products in this family have been isolated.The tetrahydroisoquinolines include potent cytotoxic agents that display a range of antitumor activities, antimicrobial activity, and other biol. properties to be discussed below depending on their structures.These natural products are classified into the saframycin, naphthylridinomycin/ bioxalomycin, and quinocarcin/ tetrazomine families of natural products.Some of these natural products have been reviewed in the literature, but this is intended to be the most comprehensive review to date.Pertinent structural, synthetic, semisynthetic, and biol. studies reported in the open literature will be covered in this review.

01 May 2001·The Journal of Organic ChemistryQ2 · CHEMISTRY

Enantioselective Synthesis of the AB-Ring System of the Antitumor Antibiotic Tetrazomine

Q2 · CHEMISTRY

Article

Author: Hopkins, Corey R. ; Wipf, Peter

The synthesis of the 1,2,3,4-tetrahydroisoquinoline moiety of tetrazomine was accomplished in 18 steps and in 3% overall yield from commercially available o-anisaldehyde. The reaction sequence utilizes a Sharpless asymmetric dihydroxylation to install the stereocenter and an intramolecular Friedel--Crafts hydroxyalkylation with an N-protected 2-oxo-acetamide to close the heterocyclic ring.

17 Apr 2001·Angewandte Chemie International EditionQ1 · CHEMISTRY

Total Synthesis of (−)-Tetrazomine and Determination of Its Stereochemistry

Q1 · CHEMISTRY

Article

Author: Scott, Jack D ; Williams, Robert M

A new method for the formation of the allylic amine precursor to an azomethine ylide 1 has been developed and exploited in an efficient 1,3-dipolar cycloaddition to afford the key tetracyclic intermediate used in the synthesis of (-)-tetrazomine (2). Bn=benzyl.

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