Enantioselective synthesis of a key "A-ring" intermediate for the preparation of 1α-fluoro vitamin D3 analogues

被引：25

作者：

Giuffredi, Guy ^{[1
]}

Bobbio, Carla ^{[1
]}

Gouverneur, Veronique ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 14期

关键词：

D O I：

10.1021/jo060516m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1 alpha-Fluoro A-ring dienol 2, a useful building block for the preparation of fluorinated vitamin D-3 analogues, was synthesized in eight steps from 4-{[tert-butyldimethylsilyl]oxy}-cyclohexanone. The most distinctive synthetic development to emerge from this new synthesis is an unprecedented substrate-controlled diastereoselective fluorodesilylation of an advanced dienylsilane intermediate. This is the first enantioselective route to compound 2 relying on the use of an electrophilic fluorinating reagent.

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页码：5361 / 5364

页数：4

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