General Method for Synthesis of Erythrinan and Homoerythrinan Alkaloids (1) : Synthesis of a Cycloerythrinan, as a Key Intermediate to Erythrina Alkaloids, by Pummerer-Type Reaction

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概要

• 論文の詳細を見る

• A new synthetic route to Erythrina alkaloids by formation of ring C utilizing a Pummerer-type intramolecular cyclization was developed. The N-(2-phenylthioethyl)-dioxopyrroline (3) was converted to 13 in five steps with satisfactory overall yield (69%) by means of [2+2] photocycloaddition followed by 1,3-anionic rearrangement as crucial reactions. Treatment of the sulfoxide (13) with trifluoroacetic anhydride gave the cyclization product, 11-phenylthioerythrinan (15), in 87% yield. This was converted to the cycloerythrinan (22) by reductive elimination of the PhS group, thus constituting a formal total synthesis of (±)-erysotrine.

• 公益社団法人日本薬学会の論文
• 1998-06-15

著者

• TSUDA YOSHISUKE

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• SANO Takehiro

  Showa College of Pharmaceutical Sciences

• TODA Jun

  Showa College of Pharmaceutical Sciences

• Toda J

  Showa Coll. Pharmaceutical Sci. Tokyo Jpn

• Takeda Kaoru

  Showa College Of Pharmaceutical Sciences

• NIIMURA Yoshihiro

  Showa College of Pharmaceutical Sciences

• Tsuda Yoshisuke

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Tsuda Y

  Faculty Of Pharmaceutical Sciences And High Technology Research Center Kobe Gakuin University

• Niimura Y

  Showa College Of Pharmaceutical Sciences

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