Synthetic Studies of Hetisan-type Aconite Alkaloids-Total Synthesis of (.+-.)-Nominine-

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  • Ｈｅｔｉｓａｎ型トリカブトアルカロイドの合成研究―（±）‐Ｎｏｍｉｎｉｎｅの全合成―
  • Hetisanガタ トリカブトアルカロイド ノ ゴウセイ ケンキュウ Nominine ノ ゼンゴウセイ
  • Total Synthesis of (±) -Nominine
  • (±) -Nominineの全合成

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Abstract

A total synthesis of (±) -nominine 1, a heptacyclic hetisan-type aconite alkaloid isolated from Aconitum sanyoense Nakai, was achieved by use of the palladium-catalyzed intramolecular α-arylation of formyl group. The synthesis is composed of forty steps starting from 1-bromo-2- (2-iodoethyl) -4-methoxybenzene 63 in 0.15% overall yield, and constitutes the first total synthesis of a hetisan-type aconite alkaloid, the sole representative aconite skeleton whose total synthesis has remained unsuccessful. The other key steps include (i) acetal ene-reaction to form the C14-C20 bond 55→56, (ii) stereoselective hydrocyanation 57→58, (iii) LiAlH4 reduction of cyano-enol silyl ether to form the N-C 6 bond 58→59, and (iv) radical cyclization from enyne precursor to construct the methylenebicyclo [2.2.2] octane framework 60→61. Completion of the synthesis was verified unambiguously by single crystal X-ray analysis of the resulting (±) -nominine to confirm its crystal structure as well as its molecular structure.

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