Synthesis of the KLMN fragment of gymnocin-A using oxiranyl anion convergent methodology

Takeo Sakai; Haruka Asano; Kyoko Furukawa; Rie Oshima; Yuji Mori

doi:10.1021/ol500788c

Synthesis of the KLMN fragment of gymnocin-A using oxiranyl anion convergent methodology

Org Lett. 2014 Apr 18;16(8):2268-71. doi: 10.1021/ol500788c. Epub 2014 Apr 9.

Authors

Takeo Sakai¹, Haruka Asano, Kyoko Furukawa, Rie Oshima, Yuji Mori

Affiliation

¹ Faculty of Pharmacy, Meijo University , Yagotoyama 150, Tempaku-ku, Nagoya 468-8503, Japan.

PMID: 24716808
DOI: 10.1021/ol500788c

Abstract

Synthesis of the KLMN fragment of gymnocin-A has been achieved by a [X + 2 + Y]-type convergent strategy involving the coupling of a K-ring triflate and an N-ring epoxy sulfone. Fusions of the L ring and the M ring were carried out by intramolecular SN2 substitution of a tertiary alcohol and reductive etherification to furnish the target molecule.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry
Dinoflagellida / chemistry
Ethers, Cyclic / chemical synthesis*
Ethers, Cyclic / chemistry
Molecular Structure
Oxidation-Reduction

Substances

Alcohols
Ethers, Cyclic
gymnocin A