Coibacins A and B: Total Synthesis and Stereochemical Revision

被引：23

作者：

Carneiro, Vania M. T. ^{[1
]}

Avila, Carolina M. ^{[1
]}

Balunas, Marcy J. ^{[2
]}

Gerwick, William H. ^{[3
,4
]}

Pilli, Ronaldo A. ^{[1
]}

机构：

[1] Univ Campinas UNICAMP, Inst Chem, BR-13084971 Campinas, SP, Brazil

[2] Univ Connecticut, Dept Pharmaceut Sci, Div Med Chem, Storrs, CT 06269 USA

[3] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA

[4] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 02期

基金：

巴西圣保罗研究基金会;

关键词：

CYANOBACTERIUM LYNGBYA-MAJUSCULA; HUMAN CANCER-CELLS; POTENT CYTOTOXIC POLYKETIDE; TUMOR AGENTS CI-920; IN-VITRO EVALUATION; CALLYSPONGIA-TRUNCATA; ALLYLIC ALCOHOLS; NATURAL-PRODUCTS; MARINE SPONGE; PD 113,270;

D O I：

10.1021/jo402339y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.

引用

页码：630 / 642

页数：13

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