Mitsunobu reaction synthetic utility

Scheme 21 shows the synthesis of a dihydrofuran derivative 86. Synthesis of this compound was described by Nam et al. [68] utilizing a furanone compound 87 synthesized by Kim et al. [61] via a similar synthetic approach as described in Scheme 17. The lactone was reduced using lithium aluminum hydride to give the diol 88 and intramolecular etherification using the Mitsunobu reaction afforded the dihydrofuran 86 in moderate yield (47%).

Workers at Sphinx [24] have published a synthetic route to a series ofhighly functionalized biphenyl compounds. The key reactions in this sequence are the biaiyl Stille and/or Suzuki couplings to form the biphenyl nucleus and the use of Mitsunobu chemistry to attach the variable side chains (Fig. 2). The illustrated route utilizes a solution-based diaryl coupling followed by on-resin Mitsunobu reactions. Although the diaiyl coupling proceeds on solid phase, this group s desire to maximize resin loading prompted them to implement the former route. 

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