Asymmetric Synthesis of Calyculin C. 1. Synthesis of the C(1)-C(25) Fragment.
We report our synthesis of the C(1)-C(25) fragment of serine/threonine phosphatase PP1 and PP2A inhibitor, calyculin C. Synthetic efforts were directed initially toward the synthesis of a spiroketal core fragment (7), which culminated in completion of the bottom half of the natural product. The synthesis of fragment 7 and subsequent elaboration relied on an allylboration strategy for introduction of chirality. The C(1)-C(8) fragment representing the potentially unstable tetraene moiety was introduced as a separate entity.
Scarlato
Gerard R.
GR
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095.
DeMattei
John A.
JA
Chong
Lee S.
LS
Ogawa
Anthony K.
AK
Lin
Mavis R.
MR
Armstrong
Robert W.
RW