Evolution of a Chemical Strategy Toward the Synthesis of Unsymmetrically Oxidized Nuphar Alkaloids

被引：1

作者：

Lacharity, Jacob J. ^{[1
]}

Zakarian, Armen ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

SYNLETT | 2019年 / 30卷 / 14期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

Nuphar thioalkaloids; hemiaminal; Stevens rearrangement; copper carbene; asymmetric alkylation; DIMERIC SESQUITERPENE THIOALKALOIDS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STRUCTURAL REQUIREMENTS; BIOLOGICAL EVALUATION; OLEFIN METATHESIS; FORMAL SYNTHESIS; PUMILUM; QUINOLIZIDINE; DERIVATIVES;

D O I：

10.1055/s-0037-1611866

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we describe the frustrations, joys, and unexpected turns experienced in our journey toward a successful strategy directed at the total synthesis of unsymmetrically oxidized Nuphar thioalkaloids. While many adjustments were made to our initial synthesis plan, our general approach to the construction of the central bis(spirothiolane) moiety remained unchanged. Specifically, each iteration of our synthesis design involved the formation of the thiaspirane motif through the stereodivergent coupling of a thietane with a metal carbenoid, followed by a Stevens-type rearrangement of the resulting sulfonium ylide. 1 Introduction 2 First-Generation Strategy 3 Second-Generation Strategy 4 Third-Generation Strategy 5 Conclusion

引用

页码：1632 / 1642

页数：11

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