The Li Group @ Lanzhou University

Home » total synthesis » Total Synthesis of Dapholdhamine B and (−)-Caldaphnidine O

Total Synthesis of Dapholdhamine B and (−)-Caldaphnidine O

JACS, DOI:10.1021/jacs.9b05641full text link

JACSDOI:10.1021/jacs.9b07558 full text link

文献汇报人:魏雁胜

汇报日期: 2019922

图文摘要:

1

2

推荐原因:

Dapholdhamine B and (−)-Caldaphnidine O 都含有八或九个相邻立体中心和三个季碳中心,而且Dapholdhamine B还有一个独特的氮杂金刚烷的结构,合成难度大。两个分子前七步的合成相同,提高了分子的合成效率。两个分子均用了氮杂Michael构建了关键的C-N键。在Dapholdhamine B合成中利用胺活化成环反应中的中间体经SN2′型的反应引入了C-9位的羟基,在其他已知方法失败的前提下通过优化在α,β-不饱和酮的α引入溴。在(−)-Caldaphnidine O合成中,利用邻二醇的氧化裂解和烷基化反应扩环,Sm(II)/Fe(III)-介导的Kagan−Molander 偶联反应构建环戊烷,用在第一个分子合成中意外发现的自由基环化构建C-N键。


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Enter your email address to follow this blog and receive notifications of new posts by email.

Join 1 other follower

%d bloggers like this: