期刊
TETRAHEDRON
卷 63, 期 28, 页码 6548-6557出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.03.022
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Two approaches for the total synthesis of the spiromacrolide retipolide E (5) are described, the first using a modified Mitsunobu reaction as key step for the formation of the strained 14-membered macrolactone, the second a nucleophilic aromatic substitution (SNAr). In the first approach an alpha-oxomacrolactone 15 was obtained, which could either be converted into ornatipolide (6) or further transformed into racemic retipolide E [(R, S)-5] by directed aldol condensation with a methyl arylpyruvate. The second approach allowed the synthesis of either racemic or enantiomerically pure retipolide E (5). In the latter case Evans' methodology was used for the introduction of stereogenic center via stereoselective alkylation. The oxazolidinone auxiliary was removed under mild conditions by exchange for 2-arylethanol 22 with Otera's distannoxane catalyst. Synthetic retipolide E allowed the identification of this biosynthetic intermediate in the fruit bodies of the North American mushroom Retiboletus retipes. (c) 2007 Elsevier Ltd. All rights reserved.
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