SYNTHESIS OF DIOXABICYCLO[3.2.1]OCTANE CORE OF THE ZARAGOZIC ACIDS

Masayoshi Tsubuki; Hiroyuki Okita; Toshio Honda

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SYNTHESIS OF DIOXABICYCLO[3.2.1]OCTANE CORE OF THE ZARAGOZIC ACIDS

机译：萨拉戈斯酸二氧杂双环[3.2.1]辛酸的合成

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Synthesis of the bicyclic core of zaragozic acids employing chiral furylglycerol(6)is described.Key steps are stereoselective construction of the C4 to C6 carbon centers by syn-dihydroxylation of alkene followed by reduction of carbonyl group in pyranone(8),introduction of ethynyl moiety as a carboxylic acid synthon at C3 by nucleophilic addition of lithium trimethylsilylacetylide to aldehyde(19),and bicyclic formation of dihydroxy ketone by ketalization,providing the 2,8-dioxabicyclo[3.2.1]octane core of zaragozic acids.

机译：描述了使用手性呋喃基甘油（6）合成zaragozic酸的双环核心的关键步骤是通过烯烃的顺式二羟基化，然后在吡喃酮中还原羰基（8），引入乙炔基来立体选择性地构建C4至C6碳中心通过将三甲基甲硅烷基乙炔锂向醛（19）亲核加成，并通过缩酮化双环形成二羟基酮，在C3处作为羧酸合成子，提供了zaragozic酸的2,8-二氧杂双环[3.2.1]辛烷核。

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《Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry》 |2006年第2期|共18页
作者
Masayoshi Tsubuki; Hiroyuki Okita; Toshio Honda;
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正文语种 eng
中图分类杂环化合物;
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1. Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 2,8-dioxabicyclo[3.2.1]octane core of squalestatins/zaragozic acids [J] . Herman O. Sintim, Hamad H. Al Mamari, Hasanain A. A. Almohseni, Beilstein journal of organic chemistry. . 2019,第1期

机译：锂化的酒石酸二甲酯二丙酮化物与未活化的烷基卤化物的烷基化及其在角鲨素/芥子酸的2,8-二氧杂双环[3.2.1]辛烷核的不对称合成中的应用
2. Enantioselective synthesis of the dioxabicyclo[3.2.1]octane core of the zaragozic acids via intramolecular Wacker-type cyclisation reactions [J] . Patrick Perlmutter, Walailak Selajerern, Filisaty Vounatsos Organic & biomolecular chemistry . 2004,第15期

机译：通过分子内Wacker型环化反应对泽拉古兹酸的二氧杂双环[3.2.1]辛烷核的对映选择性合成
3. The NARC-Based Approach to the Enantioselective Synthesis of the Zaragozic Acids. Synthesis of a C5-Alkoxycarbonyl-Substittued 2,8-Dioxabicyclo[3.2.1]octane [J] . Patrick Perlmutter, Walailak Selajarern Australian Journal of Chemistry: A Journal for the Publication of Original Research in All Branches of Chemistry . 2000,第4期

机译：Zaragozic酸的对映选择性合成的基于NARC的方法。 C5-烷氧羰基取代的2,8-二氧杂双环[3.2.1]辛烷的合成
4. Vibrational-circular-dichroism spectra of five methyl-substituted 68-dioxabicyclo3.2.1octanes [C] . Thomas Eggimann, Hal Wieser International conference on Fourier transform spectroscopy . 1992

机译：五个甲基取代的68-二恶英的二色性光谱3.2.1辛烷值
5. SYNTHESIS OF 6,8-DIOXABICYCLO(3.2.1)OCTANES; UTILIZATION AND STUDIES OF PHOSPHINOTHIOIC AMIDES. [D] . REINHARD, MICHAEL FREDERICK. 1983

机译：6,8-二氧杂双（3.2.1）辛酸的合成;光硫代酰胺的利用与研究。
6. Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 28-dioxabicyclo3.2.1octane core of squalestatins/zaragozic acids [O] . Herman O Sintim, Hamad H Al Mamari, Hasanain A A Almohseni, 2019

机译：锂化的酒石酸二甲酯二丙酮化物与未活化的烷基卤化物的烷基化及其在角鲨素/芥子酸的28-二氧杂双环3.2.1辛烷核的不对称合成中的应用
7. A diastereocontrolled synthesis of perseitol using a dioxabicyclo[3.2.1]octane chiral building block [O] . Kohei Kadota, Kunio Ogasawara, Yoshiharu Iwabuchi 2005

机译：使用二氧杂双环[3.2.1]辛烷手性结构单元非对映控制合成perseitol

SYNTHESIS OF DIOXABICYCLO[3.2.1]OCTANE CORE OF THE ZARAGOZIC ACIDS

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