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Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade
Journal article   Peer reviewed

Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade

Chao Fang, Charles S Shanahan, Daniel H Paull and Stephen F Martin
Angewandte Chemie (International ed.), Vol.51(42), pp.10596-10599
10-15-2012
PMID: 22987285

Abstract

Catalysis Cycloaddition Reaction Heterocyclic Compounds, 4 or More Rings - chemical synthesis Heterocyclic Compounds, 4 or More Rings - chemistry Molecular Structure Stereoisomerism
Sweet to the core: Enantioselective formal total syntheses of the title compounds were accomplished in 24 steps from 2-deoxy-D-ribose. The synthesis features a novel cascade of reactions culminating in an intramolecular dipolar cycloaddition to form the tricyclic core of the stemofoline alkaloids from an acyclic diazo imine intermediate.

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