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32644450535
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Total synthesis of apratoxin A has been presented in the 2nd Yamada Symposium on Key Natural Organic Molecules in Biological Systems, 2005, Hyogo, Japan.
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32644454011
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note
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Forsyth reported that thiazoline formation from the thioester of the modified cysteine derivative could not avoid elimination of the adjacent hydroxy group corresponding to the C35 position.
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12
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20444411190
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We attempted thioamide formation from N-Boc-Pro-Dtena(O-TBS)-moSer(O-TBS) -OAll using a Lawesson reagent. However, it failed because of Michael addition of the formed thioamide to the α,β-unsaturated ester. The similar result was also recently reported. Xu, Z.; Ye, T. Tetrahedron: Asymmetry 2005, 16, 1905-1912.
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32644434337
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The stereochemistry was determined by nOe observation after formation of lactone with the secondary alcohol.
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19
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32644451567
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note
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Forsyth did the aldol reaction after attachment with proline carboxylic acid. See ref 2.
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32644441803
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note
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The β-elimination of the O-Troc group was observed during silica gel column purification.
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31
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32644446375
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note
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4OAc resulted in hydrolysis of the thiazoline ring.
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33
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32644434719
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note
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The use of morpholine instead of N-methylaniline cleaved the Fmoc group on the proline ring in 2.
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