Stereoselective Synthesis of (+)-Annuionone A and (-)-Annuionone B

被引：19

作者：

Jiang, Lizhen ^{[1
]}

Liu, Xiaojing ^{[1
]}

Yuan, Po ^{[1
]}

Zhang, Yanli ^{[1
]}

Chen, Xiaochuan ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

JOURNAL OF NATURAL PRODUCTS | 2017年 / 80卷 / 04期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC ALCOHOLS; ANNUIONONE-A; STRUCTURAL REVISION; SELECTIVE SYNTHESIS; SUNFLOWER LEAVES; ACID; DERIVATIVES; OXIDATION;

D O I：

10.1021/acs.jnatprod.6b00522

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

A stereoselective synthetic approach was utilized to synthesize enantiopure annuionones A (1b) and B (2b), two ionone-type norsesquiterpenoids that both bear a 6-oxabicyclo[3.2.1]octane framework and possess allelopathic activity. A stereoselective Diels-Alder reaction based On chiral trisubstittted dienophile 20 was employed to obtain the optically active polysubstituted cyclohexane core of both natural products. Using this approach, (+)-annuionone A (1b) and (-)-annuionone B (2b) were synthesized from lactol (+)-15 in 10% overall yield.

引用

页码：805 / 812

页数：8

共 50 条

[1]

Abe F, 2000, CHEM PHARM BULL, V48, P1908, DOI 10.1248/cpb.48.1908

[2] An approach to an enantio selective synthesis of crisamicin A via a novel double Hauser-Kraus annulation strategy [J].