One-Pot, Enantioselective Synthesis Of 2,3-Dihydroazulen-6(1H)-One: A Concise Access To The Core Structure Of Cephalotaxus Norditerpenes

Keywords

Dihydroazulenone; Enantioselective; Norditerpene; One-pot; Organocatalysis

Abstract

A one-pot enantioselective synthesis of cis-substituted 2,3-dihydroazulen-6(1H)-one is described. In this cascade reaction, an organocatalyzed asymmetric Michael reaction furnishes a highly optically pure nitrobutylphenol intermediate, which is converted into an annulated tropone species by sequential oxidative dearomatization, conjugate addition, electrocyclic ring opening and nitrous acid elimination in the same reaction vessel. Both aliphatic and aromatic nitroalkenes are good substrates for the one-pot reaction, and this protocol appears to be general for various phenylpropionaldehydes as well. In the case of asymmetrically substituted phenylpropionaldehydes, the regioselectivity is likely determined by both the steric and electronic properties of the substituents. This methodology is successfully applied to the synthesis of the tricyclic core structure of Cephalotaxus norditerpenes.

Publication Date

4-1-2016

Publication Title

European Journal of Organic Chemistry

Volume

2016

Issue

12

Number of Pages

2115-2119

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1002/ejoc.201600321

Socpus ID

84963650412 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/84963650412

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