Synlett 2017; 28(07): 762-772
DOI: 10.1055/s-0036-1588146
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© Georg Thieme Verlag Stuttgart · New York

Crossing the Ring: A Journey of the Nitroso-ene Reaction

Jie Ouyang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China   Email: wangyan@sioc.ac.cn   Email: rhong@sioc.ac.cn
,
Xianwei Mi
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China   Email: wangyan@sioc.ac.cn   Email: rhong@sioc.ac.cn
,
Yan Wang*
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China   Email: wangyan@sioc.ac.cn   Email: rhong@sioc.ac.cn
,
Ran Hong*
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China   Email: wangyan@sioc.ac.cn   Email: rhong@sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 05 December 2016

Accepted after revision: 16 January 2017

Publication Date:
09 February 2017 (online)


Abstract

Recent progress in the nitroso-ene reaction indicates the potentially rich reactivity of the nitroso species. In this study, we highlight the synthetic efforts towards the construction of the aza-spirocyclic or aza-bridged ring embedded in biologically significant alkaloids via the proposed approach. Our endeavors along this direction are exemplified in the formal synthesis of (±)-cephalotaxine and the total synthesis of (–)-hosieine A.

1 Introduction

2 Aza-Spirocyclane: A Formal Synthesis of (±)-Cephalotaxine

3 Method Development

4 Aza-Bridge Ring: A Total Synthesis of (–)-Hosieine A

5 Epilogue

 
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