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

页码：2886 / 2891

页数：6

共 33 条

[1] NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE [J].

ALCARAZ, L ;

HARNETT, JJ ;

MIOSKOWSKI, C ;

MARTEL, JP ;

LEGALL, T ;

SHIN, DS ;

FALCK, JR .

TETRAHEDRON LETTERS, 1994, 35 (30) :5449-5452

[2] Natural products - antifungal agents derived from plants [J].

Arif, Tasleem ;

Bhosale, J. D. ;

Kumar, Naresh ;

Mandal, T. K. ;

Bendre, R. S. ;

Lavekar, G. S. ;

Dabur, Rajesh .

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2009, 11 (07) :621-638

[3]

Arun Kumar P, 2009, BIOORG CHEM, V37, P46

[4] Stereoselective Concise Total Synthesis of Leodomycin C and D [J].

Chinnababu, B. ;

Reddy, S. Purushotham ;

Reddy, D. Kumar ;

Rao, D. Chandra ;

Venkateswarlu, Y. .

SYNTHESIS-STUTTGART, 2012, 44 (02) :311-315

[5] Facile preparation of nucleoside-5′-carboxylic acids [J].

Epp, JB ;

Widlanski, TS .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :293-295

[6]

Evidente A, 1999, NAT TOXINS, V7, P133, DOI 10.1002/(SICI)1522-7189(199907/08)7:4<133::AID-NT60>3.0.CO

[7]

2-I

[8] Stagonolides G-I and Modiolide A, Nonenolides Produced by Stagonospora cirsii, a Potential Mycoherbicide for Cirsium arvense [J].

Evidente, Antonio ;

Cimmino, Alessio ;

Berestetskiy, Alexander ;

Andolfi, Anna ;

Motta, Andrea .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (11) :1897-1901

[9] Stagonolides B-F, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide of Cirsium arvense [J].

Evidente, Antonio ;

Cimmino, Alessio ;

Berestetskiy, Alexander ;

Mitina, Galina ;

Andolfi, Anna ;

Motta, Andrea .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (01) :31-34

[10] Total synthesis and revision of C6 stereochemistry of (+)-amphidinolide W [J].

Ghosh, AK ;

Gong, GL .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) :1085-1093

← 1 2 3 4 →