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
收藏
页码：2062 / 2065
页数：4
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