396100-83-7Relevant academic research and scientific papers
Chiral base route to cyclic polyols: Asymmetric synthesis of aminodeoxyconduritols and conduritol F
De Sousa, Simon E.,O'Brien, Peter,Pilgram, Christopher D.
, p. 8081 - 8083 (2001)
A chiral base route from a meso cyclohexene oxide to an allylic alcohol provides key intermediates for the synthesis of cyclic polyols. A Mitsunobu approach and an Overman rearrangement approach transform allylic alcohols into some aminodeoxyconduritols (95% ee). Elaboration of a chiral enone (89% ee) via (i) α-hydroxylation and (ii) stereoselective reduction completes a high yielding synthesis of the tetraacetate of conduritol F.
Optimisation of enantioselectivity for the chiral base-mediated rearrangement of bis-protected meso-4,5-dihydroxycyclohexene oxides: Asymmetric synthesis of 4-deoxyconduritols and conduritol F
De Sousa, Simon E,O'Brien, Peter,Pilgram, Christopher D
, p. 4643 - 4654 (2007/10/03)
A strategy based on diastereoselective epoxidation of a cyclohexene followed by chiral lithium amide-mediated epoxide rearrangement has been used to synthesise an allylic alcohol building block of >95% ee. The key step is the enantioselective rearrangement of a bis-protected meso-4,5-dihydroxycyclohexene oxide. A range of protecting groups and chiral base structures were surveyed in order to find the optimum protocol for high enantioselectivity. Using a tert-butyldimethylsilyloxy protecting group and a norephedrine-derived chiral base, a 93% yield of an allylic alcohol of >95% ee was achieved. To demonstrate the synthetic utility, this allylic alcohol was subsequently transformed into 4-deoxyconduritols and (+)-conduritol F.
