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Total Synthesis of (+)-Mycalamide A

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journal contribution
posted on 02.03.2006, 00:00 by Natsuko Kagawa, Masataka Ihara, Masahiro Toyota
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 δ-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.