Stereoselective Desymmetrization Methods in the Assembly of Complex Natural Molecules

  • Robert.J Sharpe

Part of the Springer Theses book series (Springer Theses)

About this book


This thesis describes the inception, design, and implementation of stereoselective desymmetrization reactions in the total synthesis of the natural products pactamycin and paspaline. In the case of pactamycin, the author develops a novel asymmetric Mannich reaction and symmetry-breaking reduction strategy to enable facile construction of the complex core architecture in fifteen steps using commercially available materials – the shortest synthesis to date. He subsequently demonstrates the flexibility of this approach in SAR investigations by highlighting the preparation of twenty-five unique pactamycin structural congeners. For paspaline, the author develops a biocatalytic desymmetrization strategy that allows the highly controlled synthesis of core stereochemistry and provides a platform for the development of new conceptual disconnections in the synthesis of "steroid-like" natural products. This thesis offers a valuable resource for students embarking on a PhD in total synthesis.


Pactamycin Paspaline Desymmetrization Natural Product Synthesis Pactamycin Analogs

Authors and affiliations

  • Robert.J Sharpe
    • 1
  1. 1.Advanced Research ChemistEastman Chemical CompanyJohnson CityUSA

Bibliographic information

  • DOI
  • Copyright Information Springer International Publishing Switzerland 2016
  • Publisher Name Springer, Cham
  • eBook Packages Chemistry and Materials Science
  • Print ISBN 978-3-319-39024-6
  • Online ISBN 978-3-319-39025-3
  • Series Print ISSN 2190-5053
  • Series Online ISSN 2190-5061
  • Buy this book on publisher's site
Industry Sectors
Chemical Manufacturing
Consumer Packaged Goods