Stereoselective construction of BC-ring unit of 19-hydroxytaxol by samarium(II) iodide-mediated double aldol cyclization

Chemistry Letters

Volumn 33, Issue 2, 2004, Pages 124-125

  Matsuo, Jun Ichi ^a,b   Ogawa, Yasuyuki ^a,b   Pudhom, Khanitha ^a,b   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

19 HYDROXYTAXOL; PACLITAXEL DERIVATIVE; SAMARIUM; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 1942423575     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.124     Document Type: Article

References (11)

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9. In order to make the structures of 12 and 13 clear, the PMB groups of these bicyclic compounds were deprotected with DDQ to lead to bridged tricyclic compounds, and their structures were determined by NOE.
10. After protection of 19-hydroxy group of 12 and 13 with TBS group, isomerization experiment by using NaOMe in MeOH-THF did not give an isomerized product which have the desired stereochemistry suited for synthesize 2.
11. -3, T = 298 K. X-ray intensities were measured on Rigaku AFC7R diffractometer with Cu Kα radiation (λ = 1.54178 Å), and R = 0.052 for 4209 observed reflections.