A practical improvement, enhancing the large-scale synthesis of (+)-discodermolide: a third-generation approach.
[reaction: see text] A significant improvement to the Penn one-gram synthesis of (+)-discodermolide (1) has been achieved. Specifically, reduction of the steric bulk of the C(11) hydroxyl protecting group permits formation of the requisite AB Wittig salt at the expense of the undesired intramolecular cyclization upon treatment with PPh(3) at ambient pressure.
Smith
Amos B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Freeze
B Scott
BS
Brouard
Ignacio
I
Hirose
Tomoyasu
T