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

ABSTRACT: 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.

SUBMITTER: Fang C

PROVIDER: S-EPMC3541778 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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

Fang Chao C Shanahan Charles S CS Paull Daniel H DH Martin Stephen F SF

Angewandte Chemie (International ed. in English) 20120917 42

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. ...[more]

PMID: 22987285

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