Stereocontrolled construction of the trans-tetrahydrofuran units in Annonaceous acetogenins

Experimental not reproducible as written


Procedure for synthesis of intermediate 2 was repeated three times at identical scale and reaction conditions as described and then modified. When followed exact same procedure as-written (12 hours), desired compound was obtained in 14% yield (confirmed by NMR) and major compound was polyhydroxy compound (reaction was periodically monitored). I modified this particular reaction by pre dissolving the olefin in ter-BuOH and then added to the reaction mixture at 0oC. The Yield was improved to 54% with reaction time was reduced to 9 hours. 

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