Literature DB >> 19856927

General synthesis of highly functionalized cyclopentane segments for the preparation of jatrophane diterpenes.

Christoph Lentsch1, Uwe Rinner.   

Abstract

Short and efficient syntheses of two diastereomeric cyclopentane segments present in most jatrophane diterpenes were achieved. Key steps are a stereoselective C-2 elongation, an RCM, and a hydroboration reaction. An orthogonal protecting group methodology makes these segments useful building blocks for diterpene synthesis.

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Year:  2009        PMID: 19856927     DOI: 10.1021/ol902221y

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


  4 in total

1.  Heliosterpenoids A and B, two Novel Jatrophane-Derived Diterpenoids with a 5/6/4/6 Ring System from Euphorbia helioscopia.

Authors:  Zhen-Peng Mai; Gang Ni; Yan-Fei Liu; Li Li; Guo-Ru Shi; Xin Wang; Jia-Yuan Li; De-Quan Yu
Journal:  Sci Rep       Date:  2017-07-07       Impact factor: 4.379

2.  Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction.

Authors:  Rita Fürst; Christoph Lentsch; Uwe Rinner
Journal:  European J Org Chem       Date:  2013-03-07

3.  Synthesis of an advanced intermediate of the jatrophane diterpene Pl-4: a dibromide coupling approach.

Authors:  Rita Fürst; Uwe Rinner
Journal:  J Org Chem       Date:  2013-08-13       Impact factor: 4.354

4.  Highly stereoselective synthesis of cyclopentanes bearing four stereocentres by a rhodium carbene-initiated domino sequence.

Authors:  Brendan T Parr; Huw M L Davies
Journal:  Nat Commun       Date:  2014-08-01       Impact factor: 14.919

  4 in total

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