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An efficient synthesis of the cyclic hexdepsipeptide destruxin B from its component residues is described that involves a [3+3] fragment coupling followed by cyclization via the azide method. A novel feature of the synthesis is the use of the Boc-hydrazide protecting group for the C-terminal N-methylalanine residue. This group serves both to inhibit facile diketopiperazine formation from the N-methylvalyl-N-methylalanine...
The influence of LiCl on deprotonation of 2-tert-butyl-2-methyl-1,3-dioxan-5-one 1 and tropinone 8 with chiral lithium amide bases is described. In most cases the enantioselectivity was much higher in the presence of 1 (or more) equivalent(s) of LiCl. In an extreme case the opposite enantiomers were obtained in the presence and in the absence of LiCl. The magnitude of LiCl effects and the optimal...
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