ASYMMETRIC TOTAL SYNTHESIS OF STAGONOLIDE F

被引：8

作者：

Chinnababu, B. ^{[1
]}

Reddy, S. Purushotham ^{[1
]}

Babu, K. Suresh ^{[1
]}

Venkateswarlu, Y. ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Nat Prod Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 19期

关键词：

Asymmetric dihydroxylation; Jacobsen's hydrolytic kinetic resolution (HKR); ring-closing metathesis (RCM); POTENTIAL MYCOHERBICIDE; STAGONOSPORA-CIRSII; MODIOLIDE;

D O I：

10.1080/00397911.2014.905602

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly convergent stereoselective total synthesis of stagonolide F is described starting from commercially available 5-hexen 1-ol using asymmetric dihydroxylation, Jacobsen's hydrolytic kinetic resolution (HKR), regioselective epoxide ring opening with vinyl Grignard reaction, esterification, and ring-closing metathesis (RCM) as key steps.

引用

收藏

页码：2886 / 2891

页数：6

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共 33 条

[11] Effect of the allylic substituents on ring closing metathesis: the total synthesis of stagonolide B and 4-epi-stagonolide B [J].

Giri, Awadut G. ;

Mondal, Mohabul A. ;

Puranik, Vedavati G. ;

Ramana, Chepuri V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (02) :398-406

[12] Plant-derived natural product research aimed at new drug discovery [J].

Itokawa, Hideji ;

Morris-Natschke, Susan L. ;

Akiyama, Toshiyuki ;

Lee, Kuo-Hsiung .

JOURNAL OF NATURAL MEDICINES, 2008, 62 (03) :263-280

[13] Novel Synthesis of Stagonolide-F, Putaminoxin and Aspinolide-A [J].

Kamal, Ahmed ;

Reddy, Papagari Venkat ;

Balakrishna, Moku ;

Prabhakar, Singaraboina .

LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (02) :143-149

[14] Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I [J].

Makabe, H ;

Kimura, Y ;

Higuchi, M ;

Konno, H ;

Murai, M ;

Miyoshi, H .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (09) :3119-3130

[15] Total synthesis of the originally proposed and revised structures of palmerolide a and isomers thereof [J].

Nicolaou, K. C. ;

Sun, Ya-Ping ;

Guduru, Ramakrishna ;

Banerji, Biswadip ;

Chen, David Y. -K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3633-3644

[16] From nature to the laboratory and into the clinic [J].

Nicolaou, K. C. ;

Chen, Jason S. ;

Dalby, Stephen M. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (06) :2290-2303

[17] Toward the Total Synthesis of the Brasilinolides: Construction of a Differentially Protected C20-C38 Segment [J].

Paterson, Ian ;

Burton, Paul M. ;

Cordier, Christopher J. ;

Housden, Michael P. ;

Muehlthau, Friedrich A. ;

Loiseleur, Olivier .

ORGANIC LETTERS, 2009, 11 (03) :693-696

[18] Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation [J].

Perepogu, Arun Kumar ;

Raman, D. ;

Murty, U. S. N. ;

Rao, Vaidya Jayathirtha .

BIOORGANIC CHEMISTRY, 2009, 37 (1-3) :46-51

[19] Metabolites from symbiotic bacteria [J].

Piel, Joern .

NATURAL PRODUCT REPORTS, 2009, 26 (03) :338-362

[20] Secondary metabolites from marine microorganisms: bacteria, protozoa, algae and fungi. Achievements and prospects [J].

Pietra, F .

NATURAL PRODUCT REPORTS, 1997, 14 (05) :453-464

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