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Synthesis of (−)-aphanorphine using a sulfur-directed aryl radical cyclization

✍ Scribed by Osamu Tamura; Takehiko Yanagimachi; Hiroyuki Ishibashi

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
442 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

Treatment of radical precursor 15a having a vinyl sulfide moiety with Bu 3 SnH in the presence of AIBN in boiling benzene afforded exclusively the 6-exo cyclization product 16a, whereas similar treatment of the exo-methylene compound 15b gave a mixture of the 6-exo cyclization product 16b and the endo-olefin product 17 formed by a 1,5-hydrogen shift. Based on these findings, the synthesis of (-)-aphanorphine was achieved using a sulfur-directed 6-exo-selective aryl radical cyclization of 22.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of (-)-Ap
ChemInform Abstract: Synthesis of (-)-Aphanorphine Using Aryl Radical Cyclization.
✍ Osamu Tamura; Takehiko Yanagimachi; Tetsuya Kobayashi; Hiroyuki Ishibashi 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 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

Synthesis of a model compound of mappici
Synthesis of a model compound of mappicine ketone based on sulfur-directed 5-exo selective aryl radical cyclization onto enamides
✍ Hiroyuki Ishibashi; Issei Kato; Yoshifumi Takeda; Osamu Tamura 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 69 KB

Enamides 10, upon treatment with Bu 3 SnH-AIBN, gave 5-exo aryl radical cyclization products 11, which were partially desulfurized to give 1-substituted dihydroisoindoles 7 and 12. This method was applied to the synthesis of a model compound 4 of mappicine ketone (1).