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Synthesis of variolin B

✍ Scribed by Abderaouf Ahaidar; David Fernández; Olga Pérez; Gerardo Danelón; Carmen Cuevas; Ignacio Manzanares; Fernando Albericio; John A. Joule; Mercedes Álvarez;

Book ID
104254165
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
123 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The total synthesis of variolin B from 4-methoxy-7-azaindole is described. The preparation of the protected amino derivative 10 and a coupling reaction of the iodo derivative 12 with 2-acetylamino-4-trimethylstannylpyrimidine are the key steps of the sequence. The use of N-tosyldichloromethanimine for the cyclisation step afforded a good entry to the 9-aminopyrido[3%,2%:4,5]pyrrolo[1,2-c]pyrimidine system. Variolin B was obtained from the triply protected tetracyclic compound 13 in two steps.

📜 SIMILAR VOLUMES

Synthesis of Variolin B.
Synthesis of Variolin B.
✍ Abderaouf Ahaidar; David Fernandez; Olga Perez; Gerardo Danelon; Carmen Cuevas; 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 56 KB 👁 1 views
Total synthesis of variolin B
Total synthesis of variolin B
✍ Regan J Anderson; Jonathan C Morris 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 110 KB

The total synthesis of the marine alkaloid variolin B has been achieved in eight steps, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroace