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Improved Synthetic Route to Enantiomerically Pure Samples of the Tetrahydropyran-2-ylacetic Acid Core Associated with the Phytotoxic Polyketide Herboxidiene

Banwell, Martin; McLeod, Malcolm; Premraj, Rajaratnam; Simpson, Gregory Wayne


The phosphine oxide (2), which embodies the tetrahydropyran-2-ylacetic acid core associated with the phytotoxic polyketide herboxidiene (1) and which is a key intermediate in a projected synthesis of this natural product, has been prepared in a highly enantio- and diastereo-selective manner. The pivotal steps in this new and improved synthesis of compound (2) involve Katsuki-Sharpless asymmetric epoxidation of the allylic alcohol (4) to give epoxide (7) and subsequent ring-cleavage of the...[Show more]

CollectionsANU Research Publications
Date published: 2000
Type: Journal article
Source: Australian Journal of Chemistry


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