Asexual and sexual reproduction are the most important biological events in the life cycle of phytopathogenic and toxigenic Fusarium and are responsible for disease epidemics.H owever,t he signaling molecules whichi nduce the asexual reproduction of Fusarium are unknown. Herein we describe the structure elucidation, including the absolute configuration, of Fusarium asexual reproduction inducer (FARI), an ew sesquiterpene derivative,b ys pectroscopic analysis,t otal synthesis,a nd conidium-inducing assays of synthetic isomers.W eh ave also uncovered the universality of FARI among Fusarium species.M oreover,amechanism-ofaction study suggested that the Gpmk1 and LaeA signaling pathwaysa re required for conidium formation induced by FARI;c onversely,t he Mgv1 of mitogen-activated protein kinase is not involved in conidium formation. FARI exhibited conidium-inducing activity at an extremely low dose and high stereoselectivity,w hichm ay suggest the presence of as tereospecific target.

RCAI-56 is a synthetic glycolipid exhibiting a potent antitumor activity by stimulation of natural killer T cells. Tetra-O-benzyl-α-carbagalactose, an important synthetic segment of RCAI-56, was stereoselectively synthesized from 1,4-dichloro-2-butene in nine steps, including the key step of organocatalytic asymmetric Diels–Alder reaction between acrolein and 1-benzyloxybutadiene.

Asexual and sexual reproduction are the most important biological events in the life cycle of phytopathogenic and toxigenic Fusarium and are responsible for disease epidemics. However, the signaling molecules which induce the asexual reproduction of Fusarium are unknown. Herein we describe the structure elucidation, including the absolute configuration, of Fusarium asexual reproduction inducer (FARI), a new sesquiterpene derivative, by spectroscopic analysis, total synthesis, and conidium-inducing assays of synthetic isomers. We have also uncovered the universality of FARI among Fusarium species. Moreover, a mechanism-of-action study suggested that the Gpmk1 and LaeA signaling pathways are required for conidium formation induced by FARI; conversely, the Mgv1 of mitogen-activated protein kinase is not involved in conidium formation. FARI exhibited conidium-inducing activity at an extremely low dose and high stereoselectivity, which may suggest the presence of a stereospecific target.