Total Synthesis of Guajava']javadimer A via Lewis Acid-Catalyzed Cascade Double Hetero-Diels-Alder Reactions

被引：2

作者：

Duan, Shengfu ^{[1
,2
]}

Zhang, Xing ^{[1
,2
]}

Li, Xiangxin ^{[1
,2
]}

Chi, Zhiyong ^{[1
,2
]}

Xie, Zhixiang ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 38期

基金：

中国国家自然科学基金;

关键词：

BIOMIMETIC SYNTHESIS; EFFICIENT SYNTHESIS; PSIDIUM-GUA[!text type='JAVA']JAVA[!/text; FLAVANONES; ALDEHYDES;

D O I：

10.1021/acs.orglett.3c02522

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of guajavadimer A, a dimeric caryophyllene-derived meroterpenoid featuring an unprecedented 4-9-6-6-6-9-4-fused ring system, is reported. Key to the approach is the construction of the pyrano[4,3,2-de]chromene core via a cascade of double hetero-Diels-Alder reactions. Practically, a 4-substituted-2,6-dihydroxybenzaldehyde dimethyl acetal serves as an effective surrogate for ortho-quinone methide, which is generated from the corresponding aldehyde and trimethyl orthoformate, with beta-caryophyllene undergoing cycloaddition to generate pyrano[4,3,2-de]chromene derivatives with excellent regioselectivity and stereoselectivity in one pot under mild conditions.

引用

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页码：6987 / 6992

页数：6

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