Synthesis of polycyclic naphthols and naphthalenes: Via tandem Ti(O i-Pr)4-promoted photoenolization Diels-Alder reaction and aromatization

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

doi:10.1039/d0qo01346c

Synthesis of polycyclic naphthols and naphthalenes: Via tandem Ti(O i-Pr)₄-promoted photoenolization Diels-Alder reaction and aromatization

Xiao Long Lu
, Baochao Yang
, Haibing He
, Shuanhu Gao

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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- A nd 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.

Original language	English
Pages (from-to)	1143-1148
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	8
Issue number	6
DOIs	https://doi.org/10.1039/d0qo01346c
State	Published - 21 Mar 2021

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10.1039/d0qo01346c

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title = "Synthesis of polycyclic naphthols and naphthalenes: Via tandem Ti(O i-Pr)4-promoted photoenolization Diels-Alder reaction and aromatization",

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- A nd 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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doi = "10.1039/d0qo01346c",

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T1 - Synthesis of polycyclic naphthols and naphthalenes

T2 - Via tandem Ti(O i-Pr)4-promoted photoenolization Diels-Alder reaction and aromatization

AU - Lu, Xiao Long

AU - Yang, Baochao

AU - He, Haibing

AU - Gao, Shuanhu

PY - 2021/3/21

Y1 - 2021/3/21

N2 - 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- A nd 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.

AB - 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- A nd 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.

UR - https://www.scopus.com/pages/publications/85103115361

U2 - 10.1039/d0qo01346c

DO - 10.1039/d0qo01346c

M3 - 文章

AN - SCOPUS:85103115361

SN - 2052-4110

VL - 8

SP - 1143

EP - 1148

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 6

ER -

Synthesis of polycyclic naphthols and naphthalenes: Via tandem Ti(O i-Pr)₄-promoted photoenolization Diels-Alder reaction and aromatization

Abstract

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