Synthesis Workshop: Synthesis of Picrotoxinin and Picrotin with Dr. Steven Crossley (Episode 27)

Описание: In this Research Spotlight episode, Dr. Steven Crossley joins us to discuss his synthesis of (–)-picrotoxinin and (–)-picrotin, which was completed in the Shenvi group.

Parent reference:
J. Am. Chem. Soc. 2020, 142, 11376–11381.
https://doi.org/10.1021/jacs.0c05042

Other references (in order of appearance):
Ann. Chim. Phys. 1811, 80, 209.; Nature 2019, 565, 454.; Nature 2014, 512, 270.; J. Biol. Chem. 2012, 287, 40224.
Biochem. Pharm. 2018, 155, 61.; JACS 2017, 139, 9637.; Nat. Prod. Rep. 2016, 33, 535.
Syntheses: Corey JACS 1979, 101, 5841.; Yamada JACS 1984, 106, 4547.; Yoshikoshi JACS 1989, 111, 3728; Trost JACS 1999,121, 233.; JACS 1996, 118, 233. Biosynthesis: Can. J. Chem. 1970, 48, 2517.
Use of carvone in total synthesis: Maimone Chem. Rev. 2017, 117, 11753.
Carvone methylation: Russ. J. Org. Chem. 2011, 47, 173.; Chem. Commun. 1996, 1369.
SOCl2 elimination: JCS, Perkin Trans. 1 1977, 1561; JOC 2008, 73, 2021.
BDSB: ACIE 2009, 48, 7899; JACS 2010, 132, 14314. NXS/HFIP/morpholine: JACS 2018, 140, 4344.
Citric acid as an enabling additive: Sharpless, B. and co. Adv. Syn. Catal. 2002, 344, 421.; ACS Cent. Sci. 2017, 3, 47.
Giberellin biosynthesis: Angew. Chem. Int. Ed. 2018, 57, 6082.
IOAc generation: EROS DOI: 10.1002/047084289X.rn00915; JACS 1972, 94, 6129; JACS 1993, 115, 8865.
Chlorination regiochemistry: Ind. Eng. Chem. 1936, 28, 333.; ACIE 2011, 50, 3362.
TFDO oxidation: J. Org. Chem. 2013, 78, 4037.; Chem. Eur. J. 2019, 25,12003.
Suárez cleavage: JACS 1993, 115, 8865; https://onlinelibrary.wiley.com/doi/1....
Mukaiyama hydration: JACS 1982, 104, 6782.; Chem. Lett. 1989, 18, 449 & 1071.; Picrotin: TL 1980, 21, 1823.