Literature DB >> 21067232

Concise total syntheses of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one.

Shibing Tang1, Xingang Xie, Xiaolei Wang, Liuer He, Ke Xu, Xuegong She.   

Abstract

Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date.

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Year:  2010        PMID: 21067232     DOI: 10.1021/jo101875w

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.

Authors:  Susanthi Jayasinghe; Phanindra K M Venukadasula; Paul R Hanson
Journal:  Org Lett       Date:  2013-12-02       Impact factor: 6.005

2.  Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419

Review 3.  Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains.

Authors:  Satya Kumar Avula; Biswanath Das; Rene Csuk; Ahmed Al-Rawahi; Ahmed Al-Harrasi
Journal:  Molecules       Date:  2020-04-20       Impact factor: 4.411

  3 in total

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