Synthesis and Reactions of Lactam Sulfonium Salts with a Sulfonio Bridgehead. II. 1,1a, 4,5,6-Pentahydro-6-oxo-2H-thiopyrano[1,6-d]-4,1-benzothiazepinium Perchlorates

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概要

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• Tricyclic benzothiazepinium salts (5) were prepared by [2^+ +4] polar cycloaddition of thionium intermediates (4A), generated from corresponding α-chloro sulfides (4) and dienes in the presence of silver perchlorate. X-Ray analysis of 5a revealed that the configuration of the thiazepinone skeleton and the dihydrothiopyran ring is cis-fused.Reactions of benzothiazepinium salts (5) with NaBH_4 or NaH afforded 3,6-epithiobenzazocinone derivatives (9) in high yields by [2,3]-sigmatropic rearrangement of an ylide intermediate (11). The stereochemistry of epithiobenzazocinone (9a) was determined by the nuclear Overhauser enhancement (NOE) technique and finally by X-ray analysis of the sulfoxide (10) derived from epithiobenzazocinone (9a) by m-chloroperbenzoic acid (MCPBA) oxidation. Alkylation of epithiobenzazocinone (9a) afforded 3-alkyl-3,6-epithiobenzazocinones (12) with retention of the configuration at C-3. Dihydrothiopyran derivatives (13) were obtained in good yields by SmI_2 reduction of benzothiazepinium salts (5).

• 社団法人日本薬学会の論文
• 1997-02-15

著者

• 清水 博

  東大

• 清水 博

  東大・薬

• Iwama Tetsuo

  Gifu Pharmaceutical University

• KATAOKA Tadashi

  Gifu Pharmaceutical University

• NAKAMURA Yoshihide

  Gifu Pharmaceutical University

• MATSUMOTO Harutoshi

  Gifu Pharmaceutical University

• SHIMIZU Hiroshi

  Gifu Pharmaceutical University

• MURAOKA Osamu

  Kinki University, Faculty of Pharmaceutical Sciences

• TANABE Genzoh

  Kinki University, Faculty of Pharmaceutical Sciences

• Iwamura T

  Gifu Pharmaceutical Univ. Gifu Jpn

• Tanabe Genzoh

  School Of Pharmacy Kinki University

• Muraoka Osamu

  Department Of Pharmacology Osaka University School Of Medicine

• Muraoka Osamu

  School Of Pharmacy Kinki Univ.

• Muraoka Osamu

  School Of Pharmacy Kinki University

• Tanabe G

  Faculty Of Pharmaceutical Sciences Kinki University

• Muraoka O

  School Of Pharmaceutical Sciences Kinki University

• Matsumoto H

  Yamanouchi Pharmaceutical Co. Ltd. Ibaraki Jpn

• Muraoka Osamu

  Kinki Univ. Osaka Jpn

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