An aldol approach to the total synthesis of pamamycin 621 A.
Pamamycin 621A was synthesized through a convergent route, with the THF rings constructed from Evans aldols in the presence of the chiral auxiliaries without suffering racemization or elimination. The basic amino group was introduced at a late stage through reduction of an azido group with n-Bu(3)SnH, which also demonstrates for the first time the great potential of this largely forgotten reduction protocol in synthesis of multifunctional substrates.
Ren
Guo-Bao
GB
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Wu
Yikang
Y
D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D018942:Macrolides; C546656:pamamycin 621 A