Rearrangement approaches to cyclic skeletons. I. Photochemical rearrangement approaches to (.+-.)-sesquicarene and (.+-.)-sirenin,(3-6) fused-ring sesquiterpenes.

T Uyehara, J Yamada, K Ogata, T Kato

Index: Uyehara, Tadao; Yamada, Jun-ichi; Ogata, Koichi; Kato, Tadahiro Bulletin of the Chemical Society of Japan, 1985 , vol. 58, p. 211 - 216

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Citation Number: 25

Abstract

The 4-alkyl, 4-alkenyl, and 4-aryl derivatives of bicyclo [3.2. 2] nona-3, 6-dien-2-one (9) were prepared from 9 itself by ultrasound-promoted Barbier reaction followed by PCC oxidation. Photochemical transformation of the 4-(4-methyl-3-pentenyl) derivative of 9, namely 13, in THF–water gave endo-7-[exo-7-(4-methyl-3-pentenyl) bicyclo [4.1. 0] hept-2-ene] acetic acid (14). Acid 14 was converted into endo-7-methyl-exo-7-(4-methyl-3-pentenyl) bicylo [4.1. 0] ...