Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Total synthesis of the alpha-glucosidase inhibitors schulzeine A, B, and C and a structural revision of schulzeine A.

Literature DB >> 19361223

Total synthesis of the alpha-glucosidase inhibitors schulzeine A, B, and C and a structural revision of schulzeine A.

Abstract

The enantioselective total synthesis of the potent alpha-glucosidase inhibitors schulzeine A, B, and C and a revision of the proposed C20' configuration of schulzeine A are reported. The central feature of our convergent route to this family of novel marine natural products is the preparation of the common benzo[a]quinolizidine subunit through a substrate-controlled, diastereoselective Pictet-Spengler cyclocondensation.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2009 PMID： 19361223 PMCID： PMC2692646 DOI： 10.1021/ja9005755

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

7 in total

Review 1. Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin.

Authors: Vinni H Lillelund; Henrik H Jensen; Xifu Liang; Mikael Bols
Journal: Chem Rev Date: 2002-02 Impact factor: 60.622

2. Biogenetically inspired enantioselective approach to Indolo[2,3-a]- and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin.

Authors: Oriol Bassas; Núria Llor; Maria M M Santos; Rosa Griera; Elies Molins; Mercedes Amat; Joan Bosch
Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

3. Arylamide inhibitors of HIV-1 integrase.

Authors: H Zhao; N Neamati; A Mazumder; S Sunder; Y Pommier; T R Burke
Journal: J Med Chem Date: 1997-04-11 Impact factor: 7.446

4. Penasulfate A, a new alpha-glucosidase inhibitor from a marine sponge Penares sp.

Authors: Yoichi Nakao; Takashi Maki; Shigeki Matsunaga; Rob W M van Soest; Nobuhiro Fusetani
Journal: J Nat Prod Date: 2004-08 Impact factor: 4.050

5. Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei.

Authors: Kentaro Takada; Taisuke Uehara; Yoichi Nakao; Shigeki Matsunaga; Rob W M van Soest; Nobuhiro Fusetani
Journal: J Am Chem Soc Date: 2004-01-14 Impact factor: 15.419

6. Total syntheses of schulzeines B and C.

Authors: Mukund K Gurjar; Chinmoy Pramanik; Debabrata Bhattasali; C V Ramana; Debendra K Mohapatra
Journal: J Org Chem Date: 2007-07-14 Impact factor: 4.354

7. First total synthesis of a novel monoterpenoid isoquinoline alkaloid, (+/-)-alangine.

Authors: Hiromitsu Takayama; Maki Arai; Mariko Kitajima; Norio Aimi
Journal: Chem Pharm Bull (Tokyo) Date: 2002-08 Impact factor: 1.645

7 in total

5 in total

Total synthesis of the alpha-glucosidase inhibitors schulzeine A, B, and C and a structural revision of schulzeine A.

Review 1. Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin.

2. Biogenetically inspired enantioselective approach to Indolo[2,3-a]- and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin.

3. Arylamide inhibitors of HIV-1 integrase.

4. Penasulfate A, a new alpha-glucosidase inhibitor from a marine sponge Penares sp.

5. Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei.

6. Total syntheses of schulzeines B and C.

7. First total synthesis of a novel monoterpenoid isoquinoline alkaloid, (+/-)-alangine.

1. INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Review 2. Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

3. Diastereoselective nitrenium ion-mediated cyclofunctionalization: total synthesis of (+)-castanospermine.

4. An unusual reactivity of BBr(3): Accessing tetrahydroisoquinoline units from N-phenethylimides.

5. Diastereoselective synthesis of γ- and δ-lactams from imines and sulfone-substituted anhydrides.