54 (アレーン)クロム錯体を用いたジヒドロキシセルラティン酸の合成(口頭発表の部)

概要

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Serrulatane class diterpenoids, dihydroxyserrulatic acid (1), secopseudopterosins A-D (2), pseudopterosins A-D (3) and related compounds have been isolated from the leaves of Eremophila serrulate, a viscid shrub and marine sea whip Pseudopterogorgia elisabethae. Some of these natural products possess the potent anti-inflammatory and analgesic properties. For a stereo- and regioselective synthesis of these terpenoids from tetralin derivatives, the following three tactical problems are required to be solved; (1) introduction of C-1 unit at meta position (C-6) of electron donating C-8 OH group, (2) trans arrangement of two benzylic substituents (at C-1 and C-4 positions), and (3) stereocontrol between C-4 and C-11 positions. We report herein a highly selective synthesis of (±)-dihydroxyserrulatic acid (1) by utilizing some characteristic properties of (arene)chromium complexes, overcoming the above problems.
天然有機化合物討論会の論文
1990-09-25