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Literature DB >> 19067558

Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.

Takefumi Kuranaga¹, Tomohiro Shirai, Daniel G Baden, Jeffrey L C Wright, Masayuki Satake, Kazuo Tachibana.

Abstract

The first total synthesis of brevisamide (1) has been accomplished in 21 linear steps starting from cis-but-2-ene-1,4-diol. A synthetic highlight is the Suzuki-Miyaura coupling between an ether ring fragment and a dienol side chain. This result confirmed the structure of 1 isolated from the dinoflagellate Karenia brevis.

Entities: Chemical

Mesh：

Substances：

Year: 2009 PMID： 19067558 DOI： 10.1021/ol802426v

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

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Cited

7 in total

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

Authors: Aaron T Herrmann; Steven R Martinez; Armen Zakarian
Journal: Org Lett Date: 2011-06-16 Impact factor: 6.005

2. Absolute configuration of brevisamide and brevisin: confirmation of a universal biosynthetic process for Karenia brevis polyethers.

Authors: Ryan M Van Wagoner; Masayuki Satake; Andrea J Bourdelais; Daniel G Baden; Jeffrey L C Wright
Journal: J Nat Prod Date: 2010-06-25 Impact factor: 4.050

3. A Formal Total Synthesis of (-)-Brevisamide.

Authors: Amos B Smith; Noriki Kutsumura; Justin Potuzak
Journal: Tetrahedron Lett Date: 2011-04-27 Impact factor: 2.415

4. Review of Florida Red Tide and Human Health Effects.

Authors: Lora E Fleming; Barbara Kirkpatrick; Lorraine C Backer; Cathy J Walsh; Kate Nierenberg; John Clark; Andrew Reich; Julie Hollenbeck; Janet Benson; Yung Sung Cheng; Jerome Naar; Richard Pierce; Andrea J Bourdelais; William M Abraham; Gary Kirkpatrick; Julia Zaias; Adam Wanner; Eliana Mendes; Stuart Shalat; Porter Hoagland; Wendy Stephan; Judy Bean; Sharon Watkins; Tainya Clarke; Margaret Byrne; Daniel G Baden
Journal: Harmful Algae Date: 2011-01-01 Impact factor: 4.273

Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.

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

2. Absolute configuration of brevisamide and brevisin: confirmation of a universal biosynthetic process for Karenia brevis polyethers.

3. A Formal Total Synthesis of (-)-Brevisamide.

4. Review of Florida Red Tide and Human Health Effects.

5. Total synthesis of (-)-brevisin: a concise synthesis of a new marine polycyclic ether.

6. An asymmetric total synthesis of brevisamide.

7. Total synthesis of brevisamide.