Total Synthesis of (-)-Exiguolide

被引：25

作者：

Zhang, Zhigao ^{[1
,2
]}

Xie, Hengmu ^{[1
,2
]}

Li, Hongze ^{[1
,2
]}

Gao, Lu ^{[1
,2
]}

Song, Zhenlei ^{[1
,2
,3
]}

机构：

[1] Sichuan Univ, Key Lab Drug Targeting, Educ Minist, West China Hosp, Chengdu 610041, Peoples R China

[2] Sichuan Univ, West China Sch Pharm, Dept Med Chem, West China Hosp, Chengdu 610041, Peoples R China

[3] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

关键词：

WADSWORTH-EMMONS REACTION; NATURAL-PRODUCT SYNTHESIS; FORMAL TOTAL-SYNTHESIS; PRINS-CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL EVALUATION; HOMOALLYLIC ALCOHOLS; ALZHEIMERS-DISEASE; CASCADE REACTION; FACILE METHOD;

D O I：

10.1021/acs.orglett.5b02162

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise total synthesis of (-)-exiguolide has been completed in an overall 2.8% yield over 20 steps in the longest linear path. The key strategies involve (1) Prins cyclization/homobromination of dienyl alcohol with the B ring-substituted aldehyde, prepared by Prins cyclization/bromination, to construct the A ring with excellent cis-Z stereochemical control and (2) an unusual side chain installation/macrocyclization strategy featuring Sonogashira cross-coupling followed by a ring-closing metathesis reaction to deliver the target.

引用

收藏

页码：4706 / 4709

页数：4

相关论文

共 72 条

[1] A multi-center phase II study of sequential paclitaxel and bryostatin-1 (NSC 339555) in patients with untreated, advanced gastric or gastroesophageal junction adenocarcinoma [J].

Ajani, JA ;

Jiang, YX ;

Faust, J ;

Chang, BCB ;

Ho, L ;

Yao, JC ;

Rousey, S ;

Dakhil, S ;

Cherny, RC ;

Craig, C ;

Bleyer, A .

INVESTIGATIONAL NEW DRUGS, 2006, 24 (04) :353-357

[2] PKC signaling deficits: a mechanistic hypothesis for the origins of Alzheimer's disease [J].

Alkon, Daniel L. ;

Sun, Miao-Kun ;

Nelson, Thomas J. .

TRENDS IN PHARMACOLOGICAL SCIENCES, 2007, 28 (02) :51-60

[3] Formal synthesis of (-)-kendomycin featuring a prins-cyclization to construct the macrocycle [J].

Bahnck, Kevin B. ;

Rychnovsky, Scott D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :13177-13181

[4] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BAL, BS ;

CHILDERS, WE ;

PINNICK, HW .

TETRAHEDRON, 1981, 37 (11) :2091-2096

[5] Formal synthesis of (+)-SCH 351448: the Prins cyclization approach [J].

Chan, Kok-Ping ;

Ling, Yvonne Hui ;

Loh, Teck-Peng .

CHEMICAL COMMUNICATIONS, 2007, (09) :939-941

[6] Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products [J].

Chan, KP ;

Loh, TP .

ORGANIC LETTERS, 2005, 7 (20) :4491-4494

[7] Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent [J].

Chan, KP ;

Loh, TP .

TETRAHEDRON LETTERS, 2004, 45 (45) :8387-8390

[8] TOTAL SYNTHESIS OF BOTH (+)-COMPACTIN AND (+)-MEVINOLIN - A GENERAL STRATEGY BASED ON THE USE OF A SPECIAL TITANIUM REAGENT FOR DICARBONYL COUPLING [J].

CLIVE, DLJ ;

MURTHY, KSK ;

WEE, AGH ;

PRASAD, JS ;

DASILVA, GVJ ;

MAJEWSKI, M ;

ANDERSON, PC ;

EVANS, CF ;

HAUGEN, RD ;

HEERZE, LD ;

BARRIE, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3018-3028

[9] Study of the Total Synthesis of (-)-Exiguolide [J].

Cook, Cyril ;

Liron, Frederic ;

Guinchard, Xavier ;

Roulland, Emmanuel .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (16) :6728-6742

[10] Total Synthesis of (-)-Exiguolide [J].

Cook, Cyril ;

Guinchard, Xavier ;

Liron, Frederic ;

Roulland, Emmanuel .

ORGANIC LETTERS, 2010, 12 (04) :744-747

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