Alkoxycarbonylmethylation of (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline

Yasuo Takeuchi, Yoshio Kamada, Koji Nishimura, Hiromi Nishioka, Masayo Nishikawa, Kuniko Hashigaki, Masatoshi Yamato, Takashi Harayama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

As part of a series of studies on synthesis of chiral 1-alkyltetrahydroisequinolines, asymmetric synthesis of 1-alkoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (IV) was investigated. Two synthetic approaches using intermolecular and intramolecular Reformatsky-type reactions from (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline (1) were attempted, but high stereoselectivity could not be obtained. For the purpose of determining the absolute structures of the compounds (2, 3) obtained by the Reformatsky-type reactions, transformation of 3a to a chiral 1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine (14) was investigated.

Original languageEnglish
Pages (from-to)796-801
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume42
Issue number4
Publication statusPublished - 1994

Fingerprint

Quinolizines
Stereoselectivity
isoquinoline
1,2,3,4-tetrahydroisoquinoline

Keywords

  • alkoxycarbonylmethylation
  • asymmetric synthesis
  • benzo[a]quinolizine
  • diastereoselective alkylation
  • oxazolo[2,3-a]isoquinoline
  • Reformatsky reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Alkoxycarbonylmethylation of (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline. / Takeuchi, Yasuo; Kamada, Yoshio; Nishimura, Koji; Nishioka, Hiromi; Nishikawa, Masayo; Hashigaki, Kuniko; Yamato, Masatoshi; Harayama, Takashi.

In: Chemical and Pharmaceutical Bulletin, Vol. 42, No. 4, 1994, p. 796-801.

Research output: Contribution to journalArticle

Takeuchi, Y, Kamada, Y, Nishimura, K, Nishioka, H, Nishikawa, M, Hashigaki, K, Yamato, M & Harayama, T 1994, 'Alkoxycarbonylmethylation of (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline', Chemical and Pharmaceutical Bulletin, vol. 42, no. 4, pp. 796-801.
Takeuchi, Yasuo ; Kamada, Yoshio ; Nishimura, Koji ; Nishioka, Hiromi ; Nishikawa, Masayo ; Hashigaki, Kuniko ; Yamato, Masatoshi ; Harayama, Takashi. / Alkoxycarbonylmethylation of (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline. In: Chemical and Pharmaceutical Bulletin. 1994 ; Vol. 42, No. 4. pp. 796-801.
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AU - Kamada, Yoshio

AU - Nishimura, Koji

AU - Nishioka, Hiromi

AU - Nishikawa, Masayo

AU - Hashigaki, Kuniko

AU - Yamato, Masatoshi

AU - Harayama, Takashi

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AB - As part of a series of studies on synthesis of chiral 1-alkyltetrahydroisequinolines, asymmetric synthesis of 1-alkoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (IV) was investigated. Two synthetic approaches using intermolecular and intramolecular Reformatsky-type reactions from (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline (1) were attempted, but high stereoselectivity could not be obtained. For the purpose of determining the absolute structures of the compounds (2, 3) obtained by the Reformatsky-type reactions, transformation of 3a to a chiral 1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine (14) was investigated.

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