Total Synthesis and Structure-Activity Relationship Studies of the Cytotoxic Anhydrophytosphingosine Jaspine B (Pachastrissamine)

被引：9

作者：

Pashikanti, Srinath ^{[1
]}

Ukani, Rehnman ^{[1
]}

David, Sunil A. ^{[1
]}

Datta, Apurba ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, 1251 Wescoe Hall Dr, Lawrence, KS 66045 USA

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 09期

关键词：

jaspine B; stereochemistry; cytotoxic; drug development; structure-activity relationships; OXA-MICHAEL ADDITION; BIOLOGICAL EVALUATION; FORMAL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; TERMINAL ALKYNES; MARINE SPONGE; (-)-JASPINE B; D-XYLOSE; ANALOGS; DERIVATIVES;

D O I：

10.1055/s-0036-1588118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By utilizing an l-serine-derived bicyclic lactone as an advanced chiral building block, a short synthetic route to the cytotoxic marine natural product jaspine B has been developed. Targeting structure-activity relationship investigations, the synthetic route has also been utilized for the synthesis and cytotoxicity evaluation of strategically modified jaspine B analogues. In addition, a previously reported synthesis of the title natural product from our research has been reinvestigated to clarify the sterochemical assignment.

引用

页码：2088 / 2100

页数：13

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