Synthesis of the C22-C40 Domain of the Azaspiracids

Zhigao Zhang; Yong Chen; Daniel Adu-Ampratwum; Antony Akura Okumu; Nathaniel T Kenton; Craig J Forsyth

doi:10.1021/acs.orglett.6b00557

Synthesis of the C22-C40 Domain of the Azaspiracids

Org Lett. 2016 Apr 15;18(8):1824-7. doi: 10.1021/acs.orglett.6b00557. Epub 2016 Apr 4.

Authors

Zhigao Zhang¹, Yong Chen¹, Daniel Adu-Ampratwum¹, Antony Akura Okumu¹, Nathaniel T Kenton¹, Craig J Forsyth¹

Affiliation

¹ Department of Chemistry and Biochemistry, The Ohio State University , Columbus, Ohio 43210, United States.

PMID: 27043010
DOI: 10.1021/acs.orglett.6b00557

Abstract

An efficient synthesis of the C22-C40 domain of the azaspiracids is described. The synthetic route features a Nozaki-Hiyama-Kishi (NHK) coupling and chelation controlled Mukaiyama aldol reaction to access an acyclic intermediate and a double-intramolecular-hetero-Michael addition (DIHMA) to provide the FG-ring system bridged ketal.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Marine Toxins / chemical synthesis*
Marine Toxins / chemistry
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Marine Toxins
Spiro Compounds
azaspiracid

Grants and funding

R01-ES10615/ES/NIEHS NIH HHS/United States