Attempts to improve the overall stereoselectivity of the Ireland-Claisen rearrangement

Organic Letters

Volumn 11, Issue 2, 2009, Pages 409-412

  Chen, Chi Li ^a   Namba, Kosuke ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; ETHER DERIVATIVE; GALACTAL; GALACTOSE; GLUCONATE CALCIUM; HALICHONDRIN B;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

CALCIUM GLUCONATE; ETHERS, CYCLIC; GALACTOSE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 61449158804     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8027225     Document Type: Article

References (39)

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28. Strictly speaking, 3 was converted to the C27-C38 building block of halichondrin B as well as homo- and nor-halichondrin Bs, whereas 4 was converted to the C44-C53 and C44-C55 building blocks of nor- and homo-halichondrin Bs, respectively.
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30. 2/PPTS) gave a 2:1 mixture of C4/C6- and C3/C4-acetonides.
31. 2 = 1.020; final R indices [I > 2σ(I)] R1 = 0.0359, wR2 = 0.0857.
32. Strictly speaking, 7 could arise through the chairlike transition state of E-6. However, this possibility is very unlikely, because E-6 was recovered and also because the E-enriched silyl ketene acetal did not give a higher yield of 7.
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36. 4), and concentrated to afford the crude O-silyl ketene acetal.
37. This transformation was repeated on 20-g scales by Dr. Chengguo Dong and Mr. Atsushi Ueda in this laboratories.
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