Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Short Paper | Regular issue | Vol 85, No. 10, 2012, pp.2531-2541
Published online, 11th September, 2012
DOI: 10.3987/COM-12-12554
ONE-POT SYNTHESIS OF MACROCYCLIC TETRAlACTONES VIA THE SEQUENTIAL INTER- AND INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION REACTIONS OF Di-2-PYRONES WITH POLYETHYLENE GLYCOL DIMETHACRYLATES

Tetsuro Shimo,* Hideki Matsukubo, and Hui Min Zhang

*Department of Chemistry, Faculty of Engineering, Kagoshima University, Korimoto, Kagoshima 890-0065, Japan

Abstract

The sensitized photocycloaddition reactions of 6,6’-dimethyl-4,4’-[1,7-(1,4,7-trioxaheptyl)]-di-2-pyrone (1a) and 6,6’-dimethyl-4,4’-[1,10-(1,4, 7,10-tetraoxadecyl)]-di-2-pyrone (1b) with polyethylene glycol dimethacrylates (2a-d) afforded macrocyclic tetralactones containing two cyclobutane rings. The reactions of 1a with 2a-d afforded diastereomixtures of macrocyclic crown ether-type structures (3a-d and 3a’-d’) possessing 19– to 28–membered rings across the C5-C6 and C5’-C6’ double bonds of 1a. Similarly, 1b reacted with 2a-d to give the corresponding 22– to 31–membered-ring products (4a-d and 4a’-d’). A structure for the key intermediate involved in the formation of compounds 3 and 4 has been proposed.