Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy

被引：8

作者：

Du, Guangyan ^{[1
]}

Bao, Wenli ^{[1
]}

Huang, Junrong ^{[1
]}

Huang, Shuangping ^{[1
]}

Yue, Hong ^{[1
]}

Yang, Wei ^{[1
]}

Zhu, Lizhi ^{[1
]}

Liang, Zhenhao ^{[1
]}

Lee, Chi-Sing ^{[1
]}

机构：

[1] Shenzhen Univ Town, Sch Chem Biol & Biotechnol, Lab Chem Genom, Peking Univ Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 09期

基金：

中国国家自然科学基金;

关键词：

ACTIVATING-FACTOR ANTAGONISTS; DIELS-ALDER REACTION; SUZUKI MACROCYCLIZATION; ASYMMETRIC-SYNTHESIS; STRUCTURAL TOPOLOGY; PAF ANTAGONISTS; RING-SYSTEM; FUNGUS; FURANOCHROMAN; CONSTRUCTION;

D O I：

10.1021/acs.orglett.5b00586

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of the ABC-tricyclic furanochroman core of phomactin A has been accomplished by a gamma-hydroxylation approach. The C ring was established by gamma-hydroxylation of an a-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (t-BuLi) and a bulky oxygen donor (Davis reagent), which afforded the gamma-hydroxylation product selectively in 63% yield.

引用

页码：2062 / 2065

页数：4

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