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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