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 A convergent total synthesis of hemibrevetoxin B.

Literature DB >> 12822999

A convergent total synthesis of hemibrevetoxin B.

Armen Zakarian¹, Alexandre Batch, Robert A Holton.

Abstract

A convergent biomimetic synthesis of hemibrevetoxin B from d-glucal and d-arabinose utilizes an electrophile-promoted cascade anti-Baldwin cyclization of an epoxy alcohol. The epoxy alcohol arises from a palladium-catalyzed coupling of a highly functionalized organozinc compound and an alkenyl iodide, which serve as two chiral building blocks of similar size and complexity. This first successful implementation of a cascade epoxy alcohol cyclization for the synthesis of marine polycyclic ether toxins proceeds in 39 steps and 4% overall yield.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 12822999 DOI： 10.1021/ja029225v

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

Keyword Cloud
Cited

25 in total

1. Total synthesis, structure revision, and absolute configuration of (-)-brevenal.

Authors: Haruhiko Fuwa; Makoto Ebine; Andrea J Bourdelais; Daniel G Baden; Makoto Sasaki
Journal: J Am Chem Soc Date: 2006-12-27 Impact factor: 15.419

Review 2. The continuing saga of the marine polyether biotoxins.

Authors: K C Nicolaou; Michael O Frederick; Robert J Aversa
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 3. The development of endo-selective epoxide-opening cascades in water.

Authors: Christopher J Morten; Jeffery A Byers; Aaron R Van Dyke; Ivan Vilotijevic; Timothy F Jamison
Journal: Chem Soc Rev Date: 2009-09-16 Impact factor: 54.564

Review 4. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

A convergent total synthesis of hemibrevetoxin B.

1. Total synthesis, structure revision, and absolute configuration of (-)-brevenal.

Review 2. The continuing saga of the marine polyether biotoxins.

Review 3. The development of endo-selective epoxide-opening cascades in water.

Review 4. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Review 5. Enzymatic Cascade Reactions in Biosynthesis.

6. A concise asymmetric total synthesis of (+)-brevisamide.

7. Maitotoxin: An Inspiration for Synthesis.

8. Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy.

Review 9. Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.

Review 10. Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.