Total Synthesis of Immunosuppressive Mycestericin E and G Enabled by a Highly Stereoselective Nitroso-Ene Cyclization

被引：2

作者：

Zhao, Yao ^{[1
]}

Ding, Yuzhen ^{[2
,3
]}

Peng, Yalan ^{[4
]}

Wang, Yang ^{[1
]}

Han, Shiqing ^{[4
]}

Zhu, Lili ^{[3
]}

Huang, Sha-Hua ^{[1
,3
]}

Hong, Ran ^{[2
,3
]}

机构：

[1] Shanghai Inst Technol, Sch Environm & Chem Engn, Shanghai 201418, Peoples R China

[2] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med IRI, 1200 Cailun Rd, Shanghai 201203, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

[4] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 19期

基金：

中国国家自然科学基金;

关键词：

FUNGAL METABOLITES; ALDEHYDES; REARRANGEMENT; DERIVATIVES; DISCOVERY; ALCOHOLS; MYRIOCIN; BETA;

D O I：

10.1021/acs.orglett.3c01082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report describes a streamlined synthesis of immunosuppressive mycestericin E and G through a highly stereo-selective nitroso-ene cyclization in 11-12 steps using readily available materials. The stereochemical outcome in the formation of a N alpha- quaternary stereogenic center is rationalized by a trajectory based on the polar diradical intermediate and subsequent hydrogen transfer. Julia olefination offers a facile chain elongation method that presents a viable strategy for structural derivatization in future medicinal applications.

引用

页码：3497 / 3501

页数：5

共 14 条

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