A NEW APPROACH TO 1,7-DIOXASPIROUNDEC-4-ENES VIA METALLATED ALLENOL ETHERS. SYNTHESIS OF LACRIMIN A.

Article abstract of DOI:10.1016/S0040-4020(01)85578-2

Key steps in the first total synthesis of Lacrimin A (2) include (a) the use of methoxyallene as an enone-1,3-dianion equivalent; (b) the use of a new copper-catalysed migratory insertion reaction to construct a tri-substituted alkene stereoselectively; and (c) the use of a Pd(0)-catalysed coupling reaction to generate an isochromanone ring.