Synthesis of Bis-Macrocyclic HCV Protease Inhibitor MK-6325 via Intramolecular sp 2–sp 3 Suzuki–Miyaura Coupling and Ring Closing Metathesis

Synthesis of Bis-Macrocyclic HCV Protease Inhibitor MK-6325 via Intramolecular sp 2–sp 3 Suzuki–Miyaura Coupling and Ring Closing Metathesis

A practical asymmetric synthesis of the complex fused bis-macrocyclic HCV protease inhibitor MK-6325 (1) is described. Through the combination of a high yielding and low catalyst loading ring-closing metathesis (RCM) to forge the 15-membered macrocycle with an intramolecular sp 2–sp 3 Suzuki–Miyaura...

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Bibliographic Details
Published in:Organic letters Vol. 17; no. 6; pp. 1533 - 1536
Main Authors: Li, Hongmei, Scott, Jeremy P, Chen, Cheng-yi, Journet, Michel, Belyk, Kevin, Balsells, Jaume, Kosjek, Birgit, Baxter, Carl A, Stewart, Gavin W, Wise, Christopher, Alam, Mahbub, Song, Zhiguo Jake, Tan, Lushi
Format: Journal Article
Language:English
Published: American Chemical Society 20-03-2015
Online Access:Get full text
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Summary:A practical asymmetric synthesis of the complex fused bis-macrocyclic HCV protease inhibitor MK-6325 (1) is described. Through the combination of a high yielding and low catalyst loading ring-closing metathesis (RCM) to forge the 15-membered macrocycle with an intramolecular sp 2–sp 3 Suzuki–Miyaura cross-coupling to append the 18-membered macrocycle, multikilogram access to the unique and challenging architecture of MK-6325 (1) has been achieved.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00418