Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A

被引：41

作者：

Gao, Lei ^{[1
,2
,3
]}

Han, Jianguang ^{[3
]}

Lei, Xiaoguang ^{[1
,2
,3
,4
,5
]}

机构：

[1] Peking Union Med Coll, Grad Sch, Beijing 100730, Peoples R China

[2] Chinese Acad Med Sci, Beijing 100730, Peoples R China

[3] NIBS, Beijing 102206, Peoples R China

[4] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci,Minist Educ, Coll Chem & Mol Engn,Synthet & Funct Biomol Ctr,D, Beijing 100871, Peoples R China

[5] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 03期

关键词：

DIELS-ALDER REACTION; CULTIVATED MULBERRY TREE; MORUS-LHOU KOIDZ; STILBENE DERIVATIVES; NATURAL-PRODUCTS; LEWIS-ACID; STEM BARK; ALBA L; ADDUCTS; CATALYSIS;

D O I：

10.1021/acs.orglett.5b03285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective total syntheses of (-)-kuwanon X, (+)-kuwanon Y, and (+)-kuwanol A have been accomplished by using asymmetric Diels-Alder cyclo-addition promoted by chiral VANOL or VAPOL/boron Lewis acid. The biosynthesis-inspired asymmetric Diels-Alder cyclo-addition shows high exo selectivity (exo/endo = 13/1), which was unprecedented in the previous total syntheses of related prenylflavonoid Diels-Alder natural products. An acid catalyzed intramolecular ketalization process enabled a biomimetic transformation to construct the polycyclic skeleton of kuwanol A efficiently.

引用

页码：360 / 363

页数：4

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