A 16-step synthesis of the isoryanodane diterpene (+)-perseanol.

ABSTRACT: (+)-Perseanol is an isoryanodane diterpene that is isolated from the tropical shrub Persea indica¹ and has potent antifeedant and insecticidal properties. It is structurally related to (+)-ryanodine, which is a high-affinity ligand for and modulator of ryanodine receptors-ligand-gated ion channels that are critical for intracellular Ca²⁺ signalling in most multicellular organisms². Ryanodine itself modulates ryanodine-receptor-dependent Ca²⁺ release in many organisms, including mammals; however, preliminary data indicate that ryanodane and isoryanodane congeners that lack the pyrrole-2-carboxylate ester-such as perseanol-may have selective activity in insects³. Here we report a chemical synthesis of (+)-perseanol, which proceeds in 16

SUBMITTER: Han A 

PROVIDER: S-EPMC7123484 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature