19 テルペノイド合成を目的としたポリエン類の閉環反応

概要

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Directed toward the biogenetic type Synthesis of terpenoids from the polyene progenitors, the following two topics (I, II) are discussed. I. Selective C-C bond formation of Polyenes 1. Intermolecular acylation. Geraniol derivatives (4a) and farnesyl cyanide (11) are effectively acylated to give 5 (or 6) and 13 (and 14), respectively. The products 9 and 10 are expected to be the intermediate for taxin synthesis while 14 is converted to the synthetically useful intermediate (21). 2. Intramolecular acylation. For the constraction of carbon skeleton of terpenoids, 22 and 34 were treated with SnCl_4 to give 28〜30 and 35, respectively. 35 was transformed into ± mukulol (32). II. Brominative Cyclization of Polyenes 46 was found to be a new reagent for the brominative cyclization of polyenes. 48 and 49 were formed from 47 by the action of AlX_3. 46 is also effective for the terminal bromination of 47 and 50.
天然有機化合物討論会の論文
1975-10-01