Tetrahedron

An approach to taxodione involving biomimetic polyene cyclization methodology

WS Johnson, AB Shenvi, SG Boots

文献索引：Johnson, William S.; Shenvi, Ashok B.; Boots, Sharon G. Tetrahedron, 1982 , vol. 38, # 10 p. 1397 - 1404

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被引用次数: 16

摘要

A novel synthesis of 11, 12-dimethoxyabieta-8, 11, 13-triene (4), involving the biomimetic cyclization of allylic alcohol5 is described. This represents a formal total synthesis of taxodione (1), a tumor-inhibitory diterpenoid quinone methide. Treatment of the sodium salt of8 with allyl bromide gave a 91% yield of allyl ether19 which readily underwent a Claisen rearrangement to give (after methylation with dimethyl sulfate) the dimethoxy olefin21 in ...