Synthesis of Erythrina and Related Alkaloids. XXX. Photochemical Approach. (1). Synthesis of Key Intermediates to Erythrina Alkaloids by Intermolecular [2+2] Photocycloaddition Followed by 1,3-Shift

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概要

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• A novel synthetic route to Erythrina alkaloids consisting in [2+2] intermolecular photocycloaddition of the isoquinolinodioxopyrroline 4 to 2-trimethylsilyloxybutadienes and the subsequent ring enlargement reaction of the trimethylsilyloxyvinylcyclobutane 5 by thermal or tetrabutylammonium flouride(TBAF)-induced 1,3-shift was developed. The TBAF method was particularly useful, offering a good yield under mild reaction conditions. Thus, photoannulation of 4 with 1-methoxy-3-trimethylsilyloxybutadiene, followed by hydride reduction, TBAF-induced 1,3-shift, and hydrogenation gave the 7α-hydroxy-2,8-dioxoerythrinan 19 in overall 45% yield, and this product was converted, in 70% yield, into the 1,7-cycloerythrinan 24,a key intermediate for the total synthesis of Erythrina alkaloids.

• 公益社団法人日本薬学会の論文
• 1992-04-25

著者

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 佐野 武弘

  Showa College of Pharmaceutical Sciences.

• 津田 喜典

  金沢大薬

• 戸田 潤

  Showa College of Pharmaceutical Sciences

• 大島 武

  Faculty Of Pharmaceutical Sciences

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

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