Diastereoselective Formation of Tetrahydrofurans via Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of the C13-C29 Subunit of Amphidinolide N

被引：23
作者：
Trost, Barry M. [1 ]
Rey, Jullien [1 ]
机构：
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 22期
基金：
美国国家卫生研究院;
关键词：
CARIBENOLIDE-I STRUCTURES; REDOX ISOMERIZATION; ALCOHOLS; STRATEGY; DINOFLAGELLATE; MACROLIDE;
D O I：
10.1021/ol302409g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of the C13-C29 fragment of amphidinolide N is described. The synthesis relies on a new strategy involving Pd-catalyzed asymmetric allylic alkylation to generate diastereoselectively the cis- or trans-THF unit simply by varying the enantiomer of the ligand. The C19 hydroxyl-bearing stereocenter was introduced using a chelation-controlled allylation which led exclusively to a single diastereoisomer.
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页码：5632 / 5635
页数：4
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