ISSN:
1434-193X
Keywords:
Carbonates, ring-opening
;
Epoxides, ring-opening
;
Lactones
;
Reduction, diastereoselective
;
Polyalcohols
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
For preparing tris(γ-lactone) 3 the mono(γ-lactone) 6 was synthesized from the dichlorodiol 12 (99.8% ee). Bisepoxide 9 - derived from dichlorodiol 12 (99.8% ee) - was ring-opened with the Gilman cuprate from 2-lithio-1,5-hexadiene and CuI giving almost exclusively the monoepoxide 21; in five more steps, γ-lactone 30 with the same stereotriad as the target molecule 6 but a different protecting group was obtained. Monoepoxide 33 - also derived from dichlorodiol 12 - was ring-opened with the same Gilman cuprate affording compound 35. It was transformed into the correctly protected γ-lactone 6 in seven steps, key reactions being the ozonolysis 35 → 36 and the diastereoselective reduction 36 → anti-37.
Type of Medium:
Electronic Resource
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