Total synthesis of (+)-mycalamide A.
A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)3-TMSCl catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrahydropyran ring, which is the left segment, is constructed with use of a novel one-pot delta-lactonization protocol. Both segments are prepared from a common starting material, d-mannitol. These segments are then coupled and the functional groups are transformed to synthesize (+)-mycalamide A.
Kagawa
Natsuko
N
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.
Ihara
Masataka
M
Toyota
Masahiro
M
D000818:Animals; D002384:Catalysis; D008353:Mannitol / Q000737:chemistry*; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D008387:Marine Toxins; D011714:Pyrans; C059646:mycalamide A; D008353:Mannitol