Synthetic Studies of Haliclonin A: Construction of the 3-Azabicyclo[3.3.1]nonane Skeleton with a Bridge that Forms the 17-Membered Ring,Synlett

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Synthetic Studies of Haliclonin A: Construction of the 3-Azabicyclo[3.3.1]nonane Skeleton with a Bridge that Forms the 17-Membered Ring
Synlett ( IF 1.7 ) Pub Date : 2018-01-29 , DOI: 10.1055/s-0037-1609150
Satoshi Yokoshima ₁ , Tohru Fukuyama ₁ , Kensuke Orihara ₁ , Fumiki Kawagishi _{1,

2}

Affiliation

The core structure of haliclonin A, a 3-azabicyclo[3.3.1]nonane with a bridge that forms a 17-membered ring, was constructed. The synthesis features a ring-closing metathesis that constructs the macrocyclic ring, the stereoselective introduction of carbon units via the intramolecular cyclopropanation of a diazoester, the conjugate addition of an organocopper reagent, and the formation of 3-azabicyclo[3.3.1]nonane skeleton via an unexpected 1,5-hydride shift.

中文翻译：

Haliclonin A 的合成研究：3-氮杂双环 [3.3.1] 壬烷骨架的构建与形成 17 元环的桥接

构建了 haliclonin A 的核心结构，一种 3-氮杂双环 [3.3.1] 壬烷，具有形成 17 元环的桥。该合成具有构建大环的闭环复分解，通过重氮酯的分子内环丙烷化立体选择性引入碳单元，有机铜试剂的共轭加成以及3-氮杂双环[3.3.1]壬烷骨架的形成通过意外的 1,5-氢化物转变。

更新日期：2018-01-29

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