Synthesis of polycyclic naphthols and naphthalenes via tandem Ti(Oi-Pr)4-promoted photoenolization Diels–Alder reaction and aromatization

Xiao-Long Lu; Baochao Yang; Haibing He; Shuanhu Gao

doi:10.1039/D0QO01346C

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Synthesis of polycyclic naphthols and naphthalenes via tandem Ti(Oi-Pr)₄-promoted photoenolization Diels–Alder reaction and aromatization†

Xiao-Long Lu,^a Baochao Yang,^a Haibing He

*^b and Shuanhu Gao

*^ab

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China

^b Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China
E-mail: hbhe@chem.ecnu.edu.cn, shgao@chem.ecnu.edu.cn

Abstract

An efficient approach to naphthol and naphthalene scaffolds has been developed using a sequence involving tandem Ti(Oi-Pr)₄-promoted photoenolization Diels–Alder (PEDA) and aromatization reactions. Starting with photoenolizable ortho-tolualdehyde derived dienes, the sequence using sterically hindered cyclohexenone and cyclopentenone dienophiles construct naphthol- and naphthalene-fused polycyclic products, respectively. The strategy was successfully utilized to synthesize the core skeletons of the bioactive marine natural products garveatin C and exiguaquinol.

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Article information

DOI: https://doi.org/10.1039/D0QO01346C
Article type: Research Article
Submitted: 29 Oct 2020
Accepted: 01 Jan 2021
First published: 04 Jan 2021

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Org. Chem. Front., 2021,8, 1143-1148

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Synthesis of polycyclic naphthols and naphthalenes via tandem Ti(Oi-Pr)₄-promoted photoenolization Diels–Alder reaction and aromatization

X. Lu, B. Yang, H. He and S. Gao, Org. Chem. Front., 2021, 8, 1143 DOI: 10.1039/D0QO01346C

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