Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine, a time-dependent inhibitor of trypanothione reductase

TY - JOUR

T1 - Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine, a time-dependent inhibitor of trypanothione reductase

AU - Hamilton, Chris J.

AU - Fairlamb, Alan H.

AU - Eggleston, Ian M.

PY - 2002/4/3

Y1 - 2002/4/3

N2 - A regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine is described. The key steps involve the preparation of the differentially functionalised cis-3-oxo-8-bromo-9b-cyano-1,2,3,4,4a,9b-hexahydrobenzofuranyl tricyclic scaffold 14 which, following further elaboration, is coupled to the selectively protected acrylamidospermidine 5 via a Heck coupling reaction to give the pre-cyclised lunarine derivative 23.

AB - A regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine is described. The key steps involve the preparation of the differentially functionalised cis-3-oxo-8-bromo-9b-cyano-1,2,3,4,4a,9b-hexahydrobenzofuranyl tricyclic scaffold 14 which, following further elaboration, is coupled to the selectively protected acrylamidospermidine 5 via a Heck coupling reaction to give the pre-cyclised lunarine derivative 23.

UR - https://www.scopus.com/pages/publications/0036010006

U2 - 10.1039/b110149h

DO - 10.1039/b110149h

M3 - Article

AN - SCOPUS:0036010006

SN - 1472-7781

VL - 2

SP - 1115

EP - 1123

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 8

ER -