First Total Synthesis of Mosin B

The first total synthesis of mosin B and a diastereomer was accomplished using asymmetric desymmetrization of the σ-symmetric diol and the Nozaki−Hiyama−Kishi reaction as the key steps. The THF core segment was stereoselectively constructed employing a stereodivergent synthesis starting from a commo...

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Veröffentlicht in:Organic letters 2001-02, Vol.3 (3), p.429-432
Hauptverfasser: Maezaki, Naoyoshi, Kojima, Naoto, Sakamoto, Atsunobu, Iwata, Chuzo, Tanaka, Tetsuaki
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Sprache:eng
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Zusammenfassung:The first total synthesis of mosin B and a diastereomer was accomplished using asymmetric desymmetrization of the σ-symmetric diol and the Nozaki−Hiyama−Kishi reaction as the key steps. The THF core segment was stereoselectively constructed employing a stereodivergent synthesis starting from a common intermediate, 4-cyclohexene-1,2-diol, based on a desymmetrization strategy. By virtue of these synthetic results, it is suggested that the absolute configuration is 1a.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006938e