Efficient asymmetric syntheses of (+)-strictifolione

Efficient asymmetric syntheses of (+)-strictifolione
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DOI:
10.1055/s-2004-822387
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发表时间:
2004-06-18
影响因子:
2.6
通讯作者:
Müller, M
Müller, M
中科院分区:
化学4区
文献类型:
--
作者:
Enders, D;Lenzen, A;Müller, M

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The asymmetric synthesis and a formal asymmetric synthesis of (+)-strictifolione are described. As key step in both approaches the Julia-Kocienski olefination to create an E-configured alkene was used. The anti-1,3-diol moiety was synthesized by employing a SAMP-hydrazone alpha,alpha'-bisalkylation/deoxygenation protocol and the stereocentre of the lactone unit is based on an enzymatic reduction with baker's yeast. Alternatively, a lactone precursor could be efficiently synthesized by a (S)-proline catalyzed alpha-oxyamination of pent-4-enal.