C-O Ring Construction: (-)-Sclerophytin A (Morken), (+)-Dictyosphaeric Acid (Taylor), Goniothalesdiol A (Xie/She), (-)-7-Deoxyloganin (Lupton), (-)-Apicularen A (Uenishi), L-783, 277(Banwell) 100

In the course of a synthesis of (-)-sclerophytin A 3, James P. Morken of Boston College showed (J. Am. Chem. Soc. 2010, 132, 16380) that Oshima-Utimoto conditions transformed 1 into 2 with high stereo-and regiocontrol. En route to (+)-dictyosphaeric acid 6, Richard J. K. Taylor of the University of York found (Angew. Chem. Int. Ed. 2010, 49, 5574) that the intramolecular Michael cyclization of 4 proceeded smooothly to give 5. Xingang Xie and Xuegong She of Lanzhou University devised (Synlett 2010, 2283) the In-mediated cyclization of 7 with benzaldehyde, to effect an elegant synthesis of goniothalesdiol A 9. The carbene-mediated cyclization of 10 to 11 developed (Org. Lett. 2010, 12, 4836) by David W. Lupton of Monash University set the stage for the synthesis of (-)-7-deoxyloganin 12. Jun’ichi Uenishi of Kyoto Pharmaceutical University showed (Org. Lett. 2010, 12, 4160) that the Pd-mediated cyclization of 13 proceeded with high diastereocontrol. Intramolecular esterification than led to (-)-apicularen A 15. Martin G. Banwell of the Australian National University established (Heterocycles 2010, 82, 313) that LiHMDS was effective for the cyclization of the alkynyl Weinreb amide 16 to 17. Reduction and deprotection completed the synthesis of the resorcylic lactone L-783, 277 18.