Synthesis of the ABC framework of tamulamides A and B

Elizabeth H Kelley; Timothy F Jamison

doi:10.1016/j.bmc.2018.04.046

Synthesis of the ABC framework of tamulamides A and B

Bioorg Med Chem. 2018 Oct 15;26(19):5327-5335. doi: 10.1016/j.bmc.2018.04.046. Epub 2018 Apr 22.

Authors

Elizabeth H Kelley¹, Timothy F Jamison²

Affiliations

¹ Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139, United States.
² Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139, United States. Electronic address: [email protected].

Abstract

Synthesis of the fused tetrahydrofuran motif comprising the ABC rings of the marine ladder polyethers tamulamides A and B has been achieved via two different polyepoxide cascade strategies. Investigations into a triepoxide cascade under aqueous conditions revealed the importance of the electronic nature of the cascade end-group with this initial approach. Ultimately, a diepoxide cascade under basic conditions proved most successful, providing the ABC tetrahydropyran triad in 41% yield.

Keywords: Cascade reactions; Epoxide openings; Natural products; Oxygen heterocycles; Polyethers.

Publication types

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

MeSH terms

Cyclization
Epoxy Compounds / chemistry
Furans / chemistry
Marine Toxins / chemical synthesis*
Oxocins / chemical synthesis*

Substances

Epoxy Compounds
Furans
Marine Toxins
Oxocins
tamulamide A
tamulamide B
tetrahydrofuran

Grants and funding

R01 GM072566/GM/NIGMS NIH HHS/United States