Total synthesis of leustroducsin B.
A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).
Shimada
Kousei
K
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kaburagi
Yosuke
Y
Fukuyama
Tohru
T
D003115:Colony-Stimulating Factors / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D011753:Pyrones; D013302:Streptomyces / Q000737:chemistry
D003115:Colony-Stimulating Factors; D007783:Lactones; D009943:Organophosphorus Compounds; D011753:Pyrones; C084414:leustroducsin B