Enantiodivergent Formal Total Synthesis of Aspercyclide C from L-(+)-Tartaric Acid
Enantiodivergent Formal Total Synthesis of Aspercyclide C from L-(+)-Tartaric Acid
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L-( )-酒石酸对映体异构形式全合成 Aspercyclide C
DOI：
10.1055/s-0029-1218831
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发表时间：
2010
期刊：
影响因子：
--
通讯作者：
K. Bhat
中科院分区：
文献类型：
--
作者：
K. Prasad;V. Gandi;J. Nidhiry;K. Bhat
完成了环糊精C的两个对映体的对映发散形式合成。以L-(+)-酒石酸为起始原料，合成了关键保护的烯丙醇--(3R，4R)-4-(甲氧基-甲氧基)非1-烯-3-醇，再经Mitsunobu转化精制成两个对映体3-(4-甲氧基苄氧基)非1-烯-4-醇。与已知的联芳酸进行酯化，然后闭环易位和去保护完成合成。
The enantiodivergent formal syntheses of both enantiomers of aspercyclide C is accomplished. Starting from L-(+)-tartaric acid, the key protected allylic alcohol, (3R,4R)-4-(methoxy-methoxy) non-1-en-3-ol is prepared, and is then elaborated into both enantiomers of 3-(4-methoxybenzyl)oxy]non-1-en-4-ol via Mitsunobu inversion. Esterification with a known biaryl acid, followed by ring-closing metathesis and deprotection completes the syntheses.