𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Total synthesis and the absolute configuration of aurovertin b, an acute neurotoxic metabolite

✍ Scribed by Shigeru Nishiyama; Hiroaki Toshima; Hiroki Kanai; Shosuke Yamamura

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
1006 KB
Volume
44
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

Aurovartin B, a metabolitt of Calcarianori which the absolute configuration could be unambiguously confirmedl2). Our synthetic process to (-)-aurovertin B (l), summarized in Scheme I and II, was started from the readily accessible branched-chain sugar (21'3). At the outset, the tertiary hydroxyl group in 2 was benzylatcd in usual manner for ease of the following reactions, A benzyl ether (3) thus obtained was subjected to acid hydrolysis to yield a vicinal diol (I), which could be converted into an olefin (6) by sulfonylatlon and Tipson-Cohen type deoxygenation, Subsequently , selective hydrogenation of 6 using Pd on charcoal catalyst provided 7. In the next stage, 7 was successively derivatited in high yield to a conjugated ester (8) in four steps, that is, l)60% AcOH, 2lNaIO4, 3)Ph3P=C(Me)COCHe, 4)K2COJ.

For

📜 SIMILAR VOLUMES

Total Synthesis and Absolute Configurati
Total Synthesis and Absolute Configuration of the Bisanthraquinone Antibiotic BE-43472B
✍ K. C. Nicolaou; Yee Hwee Lim; Jochen Becker 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 449 KB

## Abstract **Einladung zum T**: Erstmals wurde der T‐förmige Bisanthrachinon‐Naturstoff BE‐43472B durch Totalsynthese hergestellt und seine Absolutkonfiguration aufgeklärt. Wesentliche Schritte der zentralen Kaskadensequenz sind eine Diels‐Alder‐Reaktion, die Bildung eines Halbketals und eine nucl

Total Synthesis and Absolute Configurati
Total Synthesis and Absolute Configuration of the Bisanthraquinone Antibiotic BE-43472B
✍ K. C. Nicolaou; Yee Hwee Lim; Jochen Becker 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 449 KB

## Abstract **An‐T‐biotic**: The first total synthesis of the T‐shaped bisanthraquinone natural product BE‐43472B was accomplished and its absolute configuration assigned. Key transformations in the pivotal cascade sequence include a Diels–Alder reaction, a hemiketal formation, and a nucleophilic a

ChemInform Abstract: Total Synthesis and
ChemInform Abstract: Total Synthesis and Determination of the Absolute Configuration of Frondosin B.
✍ Masayuki Inoue; Matthew W. Carson; Alison J. Frontier; Samuel J. Danishefsky 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 3 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v