Synthetic studies on the rhizoxins. II. An approach to the C10-C26 subunit using 'substrate directed' allylstannane additions to aldehydes

Article abstract of DOI:10.1016/0040-4039(96)00578-3

The construction of a C₁₀-C₂₆ fragment of the 16-membered antitumor macrolide rhizoxin has been achieved in an efficient manner. The central portion of this molecule has been prepared in enantiopure form via an iterative allylstannylation protocol starting with the ester of (R)-lactic acid. The oxazole portion of rhizoxin was attached via a samarium diiodide modified Julia coupling to generate the requisite all E triene.