著者

早川 謙二 麻生 和義 大薄 悟 兼松 顕

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集

巻号頁・発行日

vol.30, pp.387-394, 1988

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Intramolecular cycloadditions of Allenes constitute the versatile methods for the stereocontrolled synthesis of variously functionalized polycyclic compounds. Especially, intramoleclar Diels-Alder reactions using allenic dienophiles can full enjoy the merits of the unique structure of allens and proceed with extraordinary ease. On the basis of this strategy, several new synthtic methodologies were developed; (1) the intramolecular Diels-Alder reaction of allenyl ethers followed by hydration andoxidation provided a new polycyclic lactone synthesis (Scheme 1). This method was successfully applied to the total synthesis of platyphyllide 30(Scheme 5). (2) The allenyl ether bearing a substituent at C-2 position (ex.,1c,1d) underwent the tandem [2+2] cycloaddition and [3,3] sigmatropic rearrangement to produce the novel product having an bicyclo [n.3.11 carbon ring system (ex., 5c, 5d) (Scheme 2).