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Asymmetric Synthesis of (+)- and (-)-Streptenol A (1999)

Enders, Dieter ; Hundertmark, Thomas

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 751-756

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ISSN: 1434-193X

Keywords: Asymmetric synthesis ; Streptenol A ; Synthetic methods ; Natural products ; SAMP/RAMP hydrazones ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: -The asymmetric synthesis of (+)-streptenol A was carried out in ten steps and with high enantioselectivity (ee ≥ 96%). The key steps are the α-alkylation of 2,2-dimethyl-1,3-dioxan-5-one RAMP hydrazone A (1), subsequent deoxygenation and elaboration of the side chain via aldehyde B to furnish (+)-streptenol A in 23% overall yield. In analogy, the enantiomer (-)-streptenol A was synthesized using the corresponding SAMP hydrazone in 18% overall yield.

Type of Medium: Electronic Resource

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