Rearrangement Approaches to Cyclic Skeletons. IV. The Total Synthesis of (±)-Pinguisone and (±)-Deoxopinguisone Based on Photochemical [1, 3] Acyl Migration of …

T Uyehara, Y Kabasawa, T Kato

Index: Uyehara, Tadao; Kabasawa, Yasuhiro; Kato, Tadahiro Bulletin of the Chemical Society of Japan, 1986 , vol. 59, p. 2521 - 2528

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Citation Number: 15

Abstract

The total synthesis of (±)-Pinguisone (2) and (±)-deoxopinguisone (3),[5–6] fused-ring sesquiterpenes, has been achieved starting from 1-methoxy-3, 4, 5-trimethylbenzene. 1- Methoxy-4, 5, endo-8-trimethylbicyclo [2.2. 2] non-5-en-2-one (9) was prepared selectively via facial selective Diels–Alder reaction of the diene derived from the benzene and 2- chloroacrylonitrile. Ring enlargement of 9 using (CH 3) 3 SiCHN 2 and BF 3 etherate gave ...