Stereoselective Total Synthesis of the Non-Contiguous Polyketide Natural Product (–)-Dolabriferol

Naresh Gantasala, Suresh Borra, Srihari Pabbaraja

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The stereoselective total synthesis of the non-contiguous polypropionate dolabriferol has been accomplished in 17 steps, by an approach that is both divergent and convergent. The key reactions involved are enantioselective cross-aldol coupling, aldol dimerisation of propionaldehyde, Sharpless asymmetric epoxidation, regioselective epoxide opening and Yamaguchi esterification. The effects of the protecting groups on the alcohol substrate on differential reactivity in Yamaguchi esterification were noteworthy.

Original languageEnglish (US)
Pages (from-to)1230-1240
Number of pages11
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number10
DOIs
StatePublished - Mar 14 2018
Externally publishedYes

Bibliographical note

Funding Information:
G.N. acknowledges the University Grants Commission (UGC), New Delhi, for financial assistance. B.S. acknowledges the Council of Scientific and Industrial Research (CSIR), New Delhi, for financial assistance, and P.S. acknowledges the Department of Science and Technology (DST) and the Council of Scientific and Industrial Research (CSIR), New Delhi, for funding the project under budget head GAP-584.

Funding Information:
[b] Academy of Scientific and Innovative Research (AcSIR), Anusandhan Bhawan, 2-Rafi Marg, New Delhi 110001, India E-mail: srihari@iict.res.in http://www.iictindia.org/staffprofiles/staffprofile.aspx?qry=1725 Supporting information and ORCID(s) from the author(s) for this article are available on the WWW under https://doi.org/10.1002/ejoc.201701748.

Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Aldol reactions
  • Dolabriferol
  • Natural productscts
  • Polyketidesdes
  • Sharpless epoxidation
  • Total synthesis
  • Yamaguchi esterification

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