Beilstein J. Org. Chem.2009,5, No. 33, doi:10.3762/bjoc.5.33
: antitumour; bioactivity; mitomycin; mitosene; synthesis; Review
Introduction
The mitomycins pose unique challenges to the synthetic chemist. As S. Danishefsky noted, “The complexity of the problem arises from the need to accommodate highly interactive functionality in a rather compact matrix and to
directly the mitosene 111 (Scheme 31). As expected, in this case, the lithium-metal exchange occurred much faster and inverted the ratio of tetracyclic:tricyclic product from 1:10 to 4:1.
Removal of the trityl protecting group was then achieved using triethylsilane and methanesulfonic acid to give the
functionalized mitosene
W.A. Remers used a similar approach to build the quinone ring of a 1,2-disubstituted mitosene [135]. The target compound had an arrangement of the C1 and C2 substituents opposite to that found in mitomycin solvolysis products. Unfortunately, these compounds did not show any anti-tumour