Literature DB >> 21805972

Integral stereocontrolled synthesis of a spiro-norlignan, sequosempervirin A: revision of absolute configuration.

Yuji Ito1, Kazunori Takahashi, Hiromasa Nagase, Toshio Honda.   

Abstract

A novel synthetic path to sequosempervirin A was established by employing a samarium diiodide promoted intramolecular Barbier-type reaction of the lactonic iodide, in which the key structural feature, a spiro[4.5]decane ring system, could be constructed by controlling the stereochemistry of the hydroxyl group at the 8-position. The absolute configuration of natural sequosempervirin A was revised to be 4S based on this synthesis.

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Year:  2011        PMID: 21805972     DOI: 10.1021/ol2018533

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Synthetic Studies toward the Hamigerans with a 6-7-5 Tricyclic Core.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  Org Lett       Date:  2020-05-13       Impact factor: 6.005

2.  Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.

Authors:  Chao Ning; Kang-Hua Rui; Yin Wei; Min Shi
Journal:  Chem Sci       Date:  2022-06-01       Impact factor: 9.969

3.  Preparation and use of samarium diiodide (SmI(2)) in organic synthesis: the mechanistic role of HMPA and Ni(II) salts in the samarium Barbier reaction.

Authors:  Dhandapani V Sadasivam; Kimberly A Choquette; Robert A Flowers
Journal:  J Vis Exp       Date:  2013-02-04       Impact factor: 1.355

  3 in total

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