How Can We Make This: Bipolarolide D with Aidan Looby, Noah Bartfield, and Prof. Jeremy May скачать в хорошем качестве

How Can We Make This: Bipolarolide D with Aidan Looby, Noah Bartfield, and Prof. Jeremy May

In today’s first installment of “How Can We Make This?”, Aidan (@aplooby28) is joined by Ph.D. candidate Noah Bartfield (@NaOHBartfield) of Seth Herzon’s lab at Yale University and Prof. Jeremy May (@MayLabUH) at the University of Houston as they discuss the total synthesis of Bipolarolide D. References: Isolation of Bipolarolide D: Hu and Zhang. Angew. Chem. Int. Ed., 2019, 58, 12091-12095 Total Synthesis of Bipolarolides A and B: Jia ACIE, 2024, 63, e202319306 Aidan’s Route: 1 Seminal Work on Asymmetric Epoxidation: Sharpless. J. Am. Chem. Soc., 1980, 102, 5974-5976 2 Formation of alkynyl cyclopropane: Salaün. J. Org. Chem., 1980, 45, 4129-4135 3 Rearrangement of 1-(1-alkynyl)cyclopropanols to 2-cyclopentenones: Iwasawa. J. Am. Chem. Soc., 1998, 120, 3903-3914 4 Enantioselective 1,4-conjugate alkyl addition: Hoveyda. Angew. Chem. Int. Ed., 2008, 47, 7358-7362 5 Seminal Work Saegusa-Ito Oxidation: Saegusa. J. Org. Chem., 1978, 43, 1011-1013 Catalytic Modification: Larock. Tetrahedron Lett., 1995, 36, 2423-2426 6 α-bromo-α,β-cyclopentenones: Dauben. Synthetic Communications, 1988, 18, 1323-1326 7 Seminal Work on Gilman Reagents: Gilman. J. Org. Chem., 1952, 17, 1630-1634 8 Seminal Work on Luche Reduction: Luche. J. Am. Chem. Soc., 1978, 100, 2226-2227 9 Doubly decarboxylative cross-coupling: Baran. Nature, 2023, 623, 745-751 Synthesis Workshop:    • Synthesis Workshop: Electrochemical Terpen...   Noah’s Route: 1 TMS-Cp Diels-Alder precedent: Herzon, ACIE 2011, 50, 8863 2 Racemic and asymmetric synthesis of bromide: Klunder, Aust. J. Chem. 2014, 67, 1234 3 Facial selectivity precedent: Liu, Tetrahedron Lett. 1999, 40, 5593 4 Alkynylation precedent: Waser, ASC 2013, 355, 1631 5 Enantioselective Pauson-Khand: Evans ACIE 2023, 61, e202300211 6 Diastereoselectivity precedent: Krafft JACS, 1991, 113, 1963 7 Stereoretentive Negishi: Knochel ACIE 2020, 59, 320 8 Deoxygenation: Kwong Org. Chem. Front. 2014, 1, 464