The synthesis of fragment AB [C(1)-C(16)] of bryostatin 1 is described. Two aldol coupling reactions involving (i) chiral fragment A [C(1)-C(10)] with achiral B [C(11)-C(16)] and (ii) chiral fragment A1 [C(7)-C(10)] with achiral A2 [C(6)-C(1)] constitute crucial steps in which an external chiral boron reagent is used to control stereoselectivity in the creation of a new stereogenic center. This type of double asymmetric synthesis, although rarely precedented, provides a powerful means of stereocontrol over the fragment assembly.
|Original language||English (US)|
|Number of pages||9|
|Journal||Journal of Organic Chemistry|
|State||Published - 1989|
ASJC Scopus subject areas
- Organic Chemistry