Total Synthesis and Structural Revision of Lucentamycin A

被引：17

作者：

Ranatunga, Sujeewa ^{[1
]}

Tang, Chih-Hang Anthony ^{[2
]}

Hu, Chih-Chi Andrew ^{[2
]}

Del Valle, Juan R. ^{[1
]}

机构：

[1] Univ S Florida, Coll Med, H Lee Moffitt Canc Ctr & Res Inst, Drug Discovery Dept, Tampa, FL 33612 USA

[2] Univ S Florida, Coll Med, H Lee Moffitt Canc Ctr & Res Inst, Dept Immunol, Tampa, FL 33612 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 21期

关键词：

ENOLATE-CLAISEN REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; ESTER; DERIVATIVES; ASSIGNMENT; INDUCTION;

D O I：

10.1021/jo301723y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lucentamycin A is a marine-derived peptide natural product harboring a unique 4-ethylidene-3-methylproline (Emp) subunit. The proposed structure of lucentamycin A and the core Emp residue have recently been called into question through synthesis. Here, we report the first total synthesis of lucentamycin A, which confirms that the ethylidene substituent in Emp bears an E geometry, in contrast to the originally assigned Z configuration. Synthesis of the desired (E)-Emp subunit required the implementation of a novel strategy starting from Gamer's aldehyde.

引用

页码：9859 / 9864

页数：6

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