Total Synthesis of Aflastatin A.
Contributors: Evans, David A.; Shair, Matthew D.; Kishi, Yoshito
Published: 2013
Language: eng
Description: The syntheses of aflastatin A and its C3-C48 degradation fragment are described. The syntheses feature several complex diastereoselective fragment couplings, including a C35-C36 anti-Felkin-selective boron-mediated oxygenated aldol reaction, a C15-C16 Felkin-selective trityl-catalyzed Mukaiyama aldol reaction, and a C26-C27 chelate-controlled aldol reaction involving soft enolization with magnesium.
Notes: Keywords: aflastatin, aldol reaction, natural products, stereochemistry, structural revision, total synthesis.

Thesis Ph.D. Harvard University 2013