Synthesis and absolute stereochemistry of tanzawaic acid (GS-1302)

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9513-9516

  Arimoto, Hirokazu ^a   Nishimura, Kazuya ^a   Kuramoto, Makoto ^b   Uemura, Daisuke ^c  

^a SHIZUOKA UNIVERSITY   (Japan)

^b EHIME UNIVERSITY   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

Biologically active compounds; Carboxylic acids and derivatives; Stereochemistry; Stille coupling reactions

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; TANZAWAIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG ISOLATION; DRUG SYNTHESIS; HYDROGENATION; STEREOCHEMISTRY;

EID: 0032542195     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02226-6     Document Type: Article

References (12)

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5. [5] Suzuki K, Katayama E, Matsumoto T, Tsuchihashi G. Tetrahedron Lett. 1984;25:3715-3718.
6. 1H NMR study of the corresponding (R) and (S)-MTPA esters. (equation presented)
7. 1H NMR of 22.
8. 4 as a catalyst, failed, even in the presence of a tin scavenger (vide infra.).
9. [9] Farina V, Krishnamurthy V, Scott WJ, Org. React 1997; 50;1-652.
10. [10] Srogl J, Allred GD, Liebeskind LS. J. Am. Chem. Soc. 1997;119:12376-12377.
11. [11] It is unclear at this point why we see the formation of predominantly the β-isomer for entries 5, 7 and 8. The stereochemistry at C10 should control the orientation of C7 methyl group. This may influence the ease of approach of the palladium catalyst. The effects of the Liebeskind's tin scavenger on highly hindered aryl triflates is under investigation in this laboratory, results will be reported in due course. However, no coupling product from o, o'-di-sec-alkyl substituted triflate has yet been observed.
12. 3); 94% e.e.(see footnote 6)}.