Total Syntheses of Nominal and Actual Prorocentin with Dr. Raphael Zachmann скачать в хорошем качестве

Total Syntheses of Nominal and Actual Prorocentin with Dr. Raphael Zachmann

In this Research Spotlight episode, Dr. Raphael Zachmann (Fürstner group PhD, MPI) joins us to share his work on the total synthesis of nominal and actual prorocentin. This episode has an associated problem set available at https://synthesis-workshop.com/#probl.... Key paper: J. Am. Chem. Soc. 2023, 145, 2584-2595. https://doi.org/10.1021/jacs.2c12529 Additional references (in order of appearance): Isolation paper: Org. Lett. 2005, 7, 3893-3896; total synthesis of limaol: J. Am. Chem. Soc. 2021, 143, 2464−2469. Previous work: Tetrahedron Lett. 2011, 52, 1222−1224 and Symposium on the Chemistry of Natural Products, 2010; Vol. 52, pp 187−192. Session ID 32, Symposium Papers. For pioneering work on Au-catalyzed spiroketalization in total synthesis: J. Am. Chem. Soc. 2021, 143, 2464-2469 and Angew. Chem. Int. Ed. 2011, 50, 8739-8744. For the synthesis of the acrylate, see: Heterocycles 2007, 72, 327-338; Carreira-alkynylation: J. Am. Chem. Soc. 2000, 122, 1806-1807; Au-catalyzed Tsuji-type cyclization: Synlett 2016, 27, 2731-2733. For a review on stereoselektive acetal openings, see: Eur. J. Org. Chem. 2018, 6405–6431. Schaus propargylation: Org. Lett. 2011, 13, 4020-4023. Krische allylation: J. Am. Chem. Soc. 2008, 130, 14891-14899; Mukaiyama cyclization: Chem. Lett. 1990, 19, 67-70; for the mechanism of Luche reductions, see: J. Am. Chem. Soc. 1981, 103, 5454-5459. Morken bisborylation/oxidation sequence: J. Am. Chem. Soc. 2013, 135, 11222-11231. Stille protocol: Chem. Commun. 2008, 25, 2873-2875; synthesis of the vinyl iodide fragment: Tetrahedron 1996, 52, 7235-7250; synthesis of the enyne fragment: J. T. Jensen, Dissertation. Universität Dortmund, 2005. For pioneering work on Au-catalyzed spiroketalization in the total synthesis of limaol: J. Am. Chem. Soc. 2021, 143, 2464-2469 and Spirastrellolide F: Angew. Chem. Int. Ed. 2011, 50, 8739,8744. SAE: J. Am. Chem. Soc. 1980, 102, 5974-5976; sulfone chemistry: Bioorg. Med. Chem. 2015, 23, 932-943; Tetrahedron Lett. 2000, 41, 9419-9423; Helv. Chim. Acta 2003, 86, 2620-2628; OPRD 2016, 20, 1026-1033. For desulfonylations in presence of epoxides, see: Eur. J. Org. Chem. 2012, 5195–5207; J. Am. Chem. Soc. 1989, 111, 2967-2980. Synthesis 1995, 7, 868-876; Noyori-reductions with Wills catalyst: J. Org. Chem. 2013, 78, 8594-8605; similar carbonyl/olefin metatheses: J. Am. Chem. Soc. 1996, 118, 1565-1566; observation of Me-cap requirement: J. Org. Chem. 1994, 59, 4029-4031; for in-situ preparation of Tebbe´s reagent, see: J. Org. Chem. 1985, 50, 2387-2390.