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Literature DB >> 19817392

Enantioselective formal total synthesis of (+)-aspergillide C.

Abstract

An enantioselective formal total synthesis of the cytotoxic macrolide (+)-aspergillide C has been accomplished from (S)-(-)-glyceraldehyde acetonide and the Danishefsky-Kitahara diene. Strategic transformations include a hetero Diels-Alder reaction, Ferrier-type addition, and palladium-catalyzed oxidative lactonization to set key stereocenters within the dihydropyran core, followed by fragment coupling via (E)-selective Julia-Kocienski olefination.

Entities: Chemical Disease Species

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Year: 2009 PMID： 19817392 PMCID： PMC2783990 DOI： 10.1021/ol902154p

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

5 in total

1. Efficient and Facile Glycol Cleavage Oxidation Using Improved Silica Gel-Supported Sodium Metaperiodate.

Authors: Yong-Li Zhong; Tony K. M. Shing
Journal: J Org Chem Date: 1997-04-18 Impact factor: 4.354

2. New cytotoxic 14-membered macrolides from marine-derived fungus Aspergillus ostianus.

Authors: Keijiro Kito; Ryuhei Ookura; Sanae Yoshida; Michio Namikoshi; Takashi Ooi; Takenori Kusumi
Journal: Org Lett Date: 2007-12-14 Impact factor: 6.005

3. Concise total synthesis of (+)-aspergillide B.

Authors: Jian Liu; Ke Xu; Jinmei He; Ling Zhang; Xinfu Pan; Xuegong She
Journal: J Org Chem Date: 2009-07-17 Impact factor: 4.354

4. Enantioselective synthesis of aspergillide B.

Authors: Tomohiro Nagasawa; Shigefumi Kuwahara
Journal: Biosci Biotechnol Biochem Date: 2009-08-07 Impact factor: 2.043

5. Enantioselective total synthesis of aspergillide C.

Authors: Tomohiro Nagasawa; Shigefumi Kuwahara
Journal: Org Lett Date: 2009-02-05 Impact factor: 6.005

5 in total

3 in total

Enantioselective formal total synthesis of (+)-aspergillide C.

1. Efficient and Facile Glycol Cleavage Oxidation Using Improved Silica Gel-Supported Sodium Metaperiodate.

2. New cytotoxic 14-membered macrolides from marine-derived fungus Aspergillus ostianus.

3. Concise total synthesis of (+)-aspergillide B.

4. Enantioselective synthesis of aspergillide B.

5. Enantioselective total synthesis of aspergillide C.

1. Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

2. Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

3. A carbohydrate approach for the formal total synthesis of (-)-aspergillide C.