Self-consistent synthesis of the squalene synthase inhibitor zaragozic acid C via controlled oligomerization.

Self-consistent synthesis of the squalene synthase inhibitor zaragozic acid C via controlled oligomerization.
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小矛烯合酶抑制剂Zaragozic C通过受控的寡聚化的自洽合成。

DOI:
10.1021/ja808347q
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发表时间:
2008-12-24
影响因子:
15
通讯作者:
Johnson JS
Johnson JS
中科院分区:
化学1区
文献类型:
--
作者:
Nicewicz DA;Satterfield AD;Schmitt DC;Johnson JS

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Despite the prevalence of repeating subunits in chiral natural products, stereocontrolled oligomerization is a largely unexplored strategy for construction of carbon skeletal frameworks. This report describes the use of silyl glyoxylates as dipolar glycolic acid synthons in a controlled oligomerization reaction for the efficient construction of the squalene synthase inhibitor zaragozic acid C. This new methodology allows rapid, stereocontrolled formation of the carbon skeleton with a desirable protecting group scheme while minimizing functional group repair and oxidation state manipulations.
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