Total synthesis of bassiatin and its stereoisomers: Novel divergent Behavior of substrates in Mitsunobu cyclizations

被引：32
作者：
Hughes, AB
Sleebs, MM
机构：
[1] Department of Chemistry, La Trobe University, Bundoora
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 08期
关键词：
D O I：
10.1021/jo047761v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total syntheses of the morpholine-2,5-dione, Bassiatin, and its stereoisomers have been completed. A key step in the syntheses was the Mitsunobu cyclization of hydroxyacid acyclic precursors. The hydroxyacid precursors are hindered alcohols and two substrates underwent Mitsunobu cyclization with retention of configuration. The other two substrates underwent Mitsunobu cyclization with either retention or inversion of configuration depending on reaction conditions. This divergence in outcome of the Mitsunobu reaction for the same substrate depending on effective concentration is novel.
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页码：3079 / 3088
页数：10
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