Total Syntheses of FR900482
-
- Tokuyama Hidetoshi
- Graduate School of Pharmaceutical Sciences, University of Tokyo Graduate School of Pharmaceutical Sciences, Tohoku University
-
- Suzuki Masashi
- Graduate School of Pharmaceutical Sciences, University of Tokyo
-
- Fukuyamal Tohru
- Graduate School of Pharmaceutical Sciences, University of Tokyo
Bibliographic Information
- Other Title
-
- FR900482の全合成
- FR900482 ノ ゼンゴウセイ
Search this article
Abstract
This review focuses on total syntheses of antitumor antibiotic FR 900482. After a brief discussion of synthetic problems of this compound, the first racemic total synthesis of FR 900482 by Fukuyama is described, which provided some important insights for the designing synthetic route through the 8-membered N-hydroxybenzazocinone key intermediate. Then, recently disclosed total syntheses as well as formal total syntheses and synthesis of derivatives were described including Martin's formal total synthesis utilizing the Grubbs' olefin metathesis for the formation of benzazocin ring, Ciufolini's characteristic formation of benzazocin ring by a sequential reaction (intramolecular [1, 3] -dipolar cycloaddition of azide, photomediated conversion of triazorine to aziridine, and a fragmentation initiated by a homo-Brook rearrangement), Williams' total synthesis employing an intramolecular reductive amination to construct the benzazocin ring and an unusual deprotective oxidation of N-PMB group to form hydroxylamine, Paleo and Rapoport's formal synthesis taking convergent route using an epoxy α-amino acid segment derived from vinylglycin, and Fukuyama's synthetic approach using intramolecular [3+2] cycloaddition of nitrone and enantiospecific total synthesis utilizing a novel ketone synthesis and reductive intramolecular hydroxyamination.
Journal
-
- Journal of Synthetic Organic Chemistry, Japan
-
Journal of Synthetic Organic Chemistry, Japan 65 (5), 470-480, 2007
The Society of Synthetic Organic Chemistry, Japan
- Tweet
Keywords
Details 詳細情報について
-
- CRID
- 1390001205312580736
-
- NII Article ID
- 10020137904
-
- NII Book ID
- AN0024521X
-
- ISSN
- 18836526
- 00379980
-
- NDL BIB ID
- 8817833
-
- Text Lang
- ja
-
- Data Source
-
- JaLC
- NDL
- Crossref
- CiNii Articles
-
- Abstract License Flag
- Disallowed