Tosaki Shin-Ya, Nemoto Tetsuhiro, Ohshima Takashi, Shibasaki Masakatsu
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Org Lett. 2003 Feb 20;5(4):495-8. doi: 10.1021/ol0273708.
[reaction: see text] We describe a catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters. The method relies upon catalytic asymmetric epoxidation of alpha,beta-unsaturated imidazolides and amides, using lanthanide-BINOL complexes, and diastereoselective reduction of ketones. The method was applied to the enantioselective syntheses of 1,3-polyol/alpha-pyrone natural products 9a, 9b, and strictifolione (10). The absolute stereochemistry of 9a and 9b was also determined.
[反应：见正文] 我们描述了顺式和反式3,5 - 二羟基酯的催化不对称合成方法。该方法依赖于使用镧系元素 - 联萘酚配合物对α,β - 不饱和咪唑化物和酰胺进行催化不对称环氧化，以及酮的非对映选择性还原。该方法应用于1,3 - 多元醇/α - 吡喃酮天然产物9a、9b和硬叶叶酮（10）的对映选择性合成。还确定了9a和9b的绝对立体化学结构。
