A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether

被引：7

作者：

Tee, Jia Ti ^{[1
]}

Keane, Theo ^{[2
]}

Meijer, Anthony J. H. M. ^{[2
]}

Khaledi, Hamid ^{[3
]}

Abd Rahman, Noorsaadah ^{[1
]}

Chee, Chin Fei ^{[4
]}

机构：

[1] Univ Malaya, Dept Chem, Kuala Lumpur 50603, Malaysia

[2] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[3] Univ Malaya, Ctr Nat Prod & Drug Res, Kuala Lumpur 50603, Malaysia

[4] Univ Malaya, Dept Pharm, Kuala Lumpur 50603, Malaysia

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 14期

关键词：

morusalbanol A; Diels-Alder reaction; mulberry; Morus alba; biomimetic synthesis; natural products; ALDER-TYPE ADDUCTS; NATURAL-PRODUCTS; BROSIMONES;

D O I：

10.1055/s-0035-1560434

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy toward the biomimetic synthesis of morusalbanol A pentamethyl ether is described. The synthesis is based on a hydrogen-bond-assisted Diels-Alder cycloaddition between a dehydroprenyl diene and a chalcone dienophile. Selective cleavage of the ortho-methyl ether of the resulting cycloadduct allows rotation of the C3-C21 bond and subsequent intramolecular cyclization affords the pentamethyl ether of (+/-)-morusalbanol A. As with the natural product, morusalbanol A, a number of key proton and carbon signals are absent in the NMR spectra of the title product.

引用

页码：2263 / 2270

页数：8

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