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Literature DB >> 20836496

Dragmacidin E synthesis studies. Preparation of a model heptacyclic core structure.

Abstract

The conversion of a cycloheptannelated indole platform into the heptacyclic core structure of dragmacidin E proceeded over nine steps. Key sequences include a cyclocondensation to form an intermediate dihydropyrazinone ring and the conversion of a cyclic urea into the cyclic guanidine of the target.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2010 PMID： 20836496 PMCID： PMC2952717 DOI： 10.1021/ol1018008

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

16 in total

1. A Catalytic Asymmetric Synthesis of Tubifolidine.

Authors: Satoshi Shimizu; Ken Ohori; Takayoshi Arai; Hiroaki Sasai; Masakatsu Shibasaki
Journal: J Org Chem Date: 1998-10-16 Impact factor: 4.354

2. The total synthesis of (+)-dragmacidin F.

Authors: Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal: J Am Chem Soc Date: 2004-08-11 Impact factor: 15.419

3. Total synthesis of cribrostatin IV: fine-tuning the character of an amide bond by remote control.

Authors: Collin Chan; Richard Heid; Shengping Zheng; Jinsong Guo; Bishan Zhou; Takeshi Furuuchi; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

4. Dragmacidins: new protein phosphatase inhibitors from a southern australian deep-water marine sponge, spongosorites sp

Authors:
Journal: J Nat Prod Date: 1998-05 Impact factor: 4.050

5. Enantioselective synthesis of marine indole alkaloid hamacanthin B.

Authors: Biao Jiang; Cai-Guang Yang; Jun Wang
Journal: J Org Chem Date: 2002-02-22 Impact factor: 4.354

6. Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin f from a single enantiomer of quinic Acid.

Authors: Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal: J Am Chem Soc Date: 2005-04-27 Impact factor: 15.419

7. A stereospecific total synthesis of d,l-saxitoxin.

Authors: H Tanino; T Nakata; T Kaneko; Y Kishi
Journal: J Am Chem Soc Date: 1977-04-13 Impact factor: 15.419

8. Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment.

Authors: Ken S Feldman; Paiboon Ngernmeesri
Journal: Org Lett Date: 2005-11-24 Impact factor: 6.005

Review 9. A unified synthetic approach to the pyrazinone dragmacidins.

Authors: Neil K Garg; Brian M Stoltz
Journal: Chem Commun (Camb) Date: 2006-07-18 Impact factor: 6.222

10. First total synthesis of dragmacidin A via indolylglycines.

Authors: T Kawasaki; H Enoki; K Matsumura; M Ohyama; M Inagawa; M Sakamoto
Journal: Org Lett Date: 2000-09-21 Impact factor: 6.005

3 in total

1. Total synthesis of (±)-dragmacidin E.

Authors: Ken S Feldman; Paiboon Ngernmeesri
Journal: Org Lett Date: 2011-09-29 Impact factor: 6.005

2. Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors: Yuyong Ma; Saptarshi De; Chuo Chen
Journal: Tetrahedron Date: 2015-02-25 Impact factor: 2.457

3. Total Synthesis of (±)-Dragmacidin E: Problems Solved and Lessons Learned.

Authors: Ken S Feldman; Paiboon Ngernmeesri
Journal: Synlett Date: 2012-08 Impact factor: 2.454

3 in total