Santikorn Chaimanee, Manat Pohmakotr, Chutima Kuhakarn, Vichai Reutrakul and Darunee Soorukram
Org. Biomol. Chem., 2017,15, 3985-3994
DOI:
10.1039/C7OB00749C,
Paper
The first asymmetric synthesis of ent-fragransin C1 was reported. The key step involves an intramolecular C–O bond formation (furan ring formation) via chemoselective generation of the benzylic carbocation leading to the 2,3-anti-3,4-syn-4,5-anti-tetrahydrofuran moiety as a single diastereomer in good yield. Our synthesis confirms that ent-fragransin C1 possesses 2R,3R,4S,5S configurations.