Cl
Br
Kumepaloxane
- The biosynthesis of halogenated marine natural products:
as electrophiles rather
2) isms have enzymes called haloperoxidases that convert
3) mes proposed for some halogenated natural products,
.1 INTRODUCTION: ADDITIONS TO ALKENES
1) Some of their halogens appear to have been introduced
than as Lewis bases or nucleophiles, which is their character when they are
solutes in seawater.
Many marine organ
nucleophilic iodide, bromide, or chloride anions into electrophilic species that
react like I+, Br+ or Cl+.
In the biosynthetic sche
positive halogen intermediates are attacked by electrons from the π bond of an
alkene or alkyne in an addition reaction.
8
CC + A B addition A CCB
CC
H CCX
H CCOSO 3 H
H CCOH
XX X CCX
H OH
H OSO 3 H
H X
Alkene
Alkyl halide
(Section 8.2, 8.3, and 10.9)
Alkyl hydrogen sulfate
(Section 8.4)
Alcohol
(Section 8.5)
Dihaloakane
(Section 8.6, 8.7)
HA (cat.)
