Total synthesis of an enantiomeric pair of FR980482. 2. Syntheses of the aromatic and the optically active aliphatic segments

Tetrahedron

Volumn 53, Issue 30, 1997, Pages 10239-10252

  Yoshino, Toshiharu ^a   Nagata, Yuriko ^a   Itoh, Etsuko ^a   Hashimoto, Masaru ^a   Katoh, Tadashi ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030788634     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00651-0     Document Type: Article

References (32)

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3. c) Katoh, T., Yoshino, T., Nagata, Y., Nakatani, S., Terashima, S., ibid., 1996, 37, 3479-3482.
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29. After purification by column chromatography on silica gel, the aliphatic segment 5 was immediately used for the next coupling reaction 21 with the aromatic segment 4 due to its instability.
30. When the corresponding mesylate and iodide were used as substrates for the subsequent coupling reaction with the aromatic segment 4, 21 none of the desired product was obtained and the unreacted starting material was always recovered. To our delight, the triflate 5 was found to serve as an excellent electophile for the objective coupling reaction. 21 For recent examples for the usefulness of some trifrate derivatives as good electrophiles, see, a) Fairbanks, A. J., Fleet, G. W. J., Tetrahedron, 1995, 51, 3881-3894.
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