A Unified Approach for the Assembly of Atisine‐ and Hetidine‐type Diterpenoid Alkaloids: Total Syntheses of Azitine and the Proposed Structure of Navirine C,Angewandte Chemie International Edition

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A Unified Approach for the Assembly of Atisine‐ and Hetidine‐type Diterpenoid Alkaloids: Total Syntheses of Azitine and the Proposed Structure of Navirine C
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-04-26 , DOI: 10.1002/anie.201803018
Jie Liu ₁ , Dawei Ma ₁

Affiliation

A tetracyclic dinitrile was synthesized in twelve steps from cyclohex‐2‐en‐1‐one by using a chelation‐triggered conjugate addition to a γ‐hydroxy‐substituted α,β‐unsaturated nitrile and an oxidative dearomatization/Diels–Alder cycloaddition cascade as the key steps. The first total synthesis of azitine (in 17 steps) was achieved through a simple reductive cyclization of this intermediate and subsequent transformations while the total synthesis of the proposed structure of navirine C (in 19 steps) was accomplished by a hydrogen‐atom‐transfer reaction of the tetracyclic dinitrile, Pd/C‐catalyzed reductive cyclization, and subsequent functional group manipulation.

中文翻译：

Atisine和Hetidine型二萜生物碱组装的统一方法：Azitine的总合成和Navirine C的拟议结构

通过从螯合触发的共轭物加成到γ-羟基取代的α，β-不饱和腈和氧化脱芳香化/ Diels-Alder环加成级联反应中，从螯合2-en-1一步十二步合成了四环二腈关键步骤。通过该中间体的简单还原环化和随后的转化，实现了首个叠氮基氮的全合成（共17个步骤），而通过氢原子转移反应完成了拟议的萘维林C结构的全合成（共19个步骤）。四环二腈的合成，Pd / C催化的还原环化以及随后的官能团操纵。

更新日期：2018-04-26

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