Literature DB >> 19928780

Synthesis of the macrocyclic core of iriomoteolide 3a.

Chada Raji Reddy1, Gajula Dharmapuri, Nagavaram Narsimha Rao.   

Abstract

The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.

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Year:  2009        PMID: 19928780     DOI: 10.1021/ol9025183

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


  3 in total

1.  Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates.

Authors:  Olga Lavinda; Collin H Witt; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-15       Impact factor: 15.336

2.  Iriomoteolides: novel chemical tools to study actin dynamics.

Authors:  A Unzue; R Cribiú; M M Hoffman; T Knehans; K Lafleur; A Caflisch; C Nevado
Journal:  Chem Sci       Date:  2018-04-03       Impact factor: 9.825

3.  Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C 2-symmetric building block: a strategy for the synthesis of decanolide natural products.

Authors:  Bernd Schmidt; Oliver Kunz
Journal:  Beilstein J Org Chem       Date:  2013-11-18       Impact factor: 2.883

  3 in total

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