Total Synthesis of Hamigerans: Part 1. Development of Synthetic Technology for the Construction of Benzannulated Polycyclic Systems by the Intramolecular Trapping of Photogenerated Hydroxy-o-quinodimethanes and Synthesis of Key Building Blocks

摘要

A recent report disclosed the structures of a series of compounds isolated from the poecilosclerid sponge Hamigera tarangaensis Bergquist & Fromont (family Anchinoidae, syn. Phorbasidae) from the Hen and Chicken Islands off the coast of New Zealand. Termed hamigerans (e.g. 1-4), these natural products contain a unique carbon skeleton in which a substituted aromatic uncleus is fused onto a [4.3.0] carbocyclic system that contains three or four stereogenic centers and features an isopropyl group.