A diastereo- and enantioselective acylation-reduction sequence of a vinylogous urethane lactone silylketene acetal sets the initial stereocenter in this approach towards the C9-C18 fragment of okadaic acid. The remainder of the stereocenters are installed via a silyl cuprate conjugate addition trapping sequence, and a lactol is transformed to a tetrahydrofuran by addition of a propargyl aluminum species. A novel tetrabydrofuran ring opening reaction utilizing dimethyl boron bromide is also illustrated.
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Dankwardt et al. (1998) studied this question.
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