942133-09-7Relevant articles and documents
Modular total synthesis of archazolid A and B
Menche, Dirk,Hassfeld, Jorma,Li, Jun,Mayer, Kerstin,Rudolph, Sven
supporting information; experimental part, p. 7220 - 7229 (2010/02/17)
(Chemical Equation Presented) A modular total synthesis of the potent V-ATPase inhibitors archazolid A and B is reported. The convergent preparation was accomplished by late-stage diversification of joint intermediates. Key synthetic steps involve asymmetric boron-mediated aldol reactions, two consecutive Still-Gennari olefinations to set the characteristic (Z,Z)-diene system, a Brown crotyboration, and a diastereo-selective aldol condensation of highly elaborate intermediates. For macrocyclization, both an HWE reaction and a Heck coupling were successfully employed to close the 24-membered macrolactone. During the synthetic campaign, a generally useful protocol for an E-selective Heck reaction of nonactivated alkenes and a method for the direct nucleophilic displacement of the Abiko-Masamune auxiliary with sterically hindered nucleophiles were developed. The expedient and flexible strategy will enable further SAR studies of the archazolids and more detailed evaluations of target-inhibitor interactions. 2009 American Chemical Society.
Total synthesis of archazolid A
Menche, Dirk,Hassfeld, Jorma,Li, Jun,Rudolph, Sven
, p. 6100 - 6101 (2008/02/08)
The archazolids are complex polyketides isolated from the myxobacterium Archangium gephyra and are potent inhibitors of vacuolar type ATPases. Herein, we report the first total synthesis of archazolid A, which establishes unequivocally the relative and ab
