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0: Readings

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Sep 23, 2024
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- 1: Retrosynthetic Analysis

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All of the reading assignments from journals can be found here.

Week 1

Misassigned Structures: Angew. Chem. Int. Ed., 2005, 44, 1012-1044.
History of ChemDraw: Angew. Chem. Int. Ed., 2014, 53, 11140-11145.
Diversity Oriented Synthesis: Angew. Chem. Int. Ed., 2004, 43, 46-58.
Green Chemistry: Acc. Chem. Res., 2002, 35, 686-694.
Redox Economy: Angew. Chem. Int. Ed., 2009, 48, 2854-2867.
Ideal Synthesis: J. Org. Chem., 2010, 75, 4657-4673.
Scalable Synthesis: Nat. Prod. Rep., 2014, 31, 419-432.
Umpolung Chemistry: Angew. Chem. Int. Ed., 1979, 18, 239-336.
Chiral Pool Retrosynthesis - Quinic Acid: Tetrahedron Lett., 1986, 27, 5071-5074.
Zaragosic Acid C: J. Am. Chem. Soc., 2008, 130, 17281-17283.
Asymmetric Ammonia Synthon: J. Org. Chem., 1986, 51, 2820-2822.; J. Org. Chem., 1992, 57, 2114-2121.
Oxidative Kinetic Resolution Example: Angew. Chem. Int. Ed., 2008, 47, 3755-3758.

Quinine

Stork's Synthesis: J. Am. Chem. Soc., 2001, 123, 3239-3242.
Historical Overview: Angew. Chem. Int. Ed., 2007, 46, 1378-1413.
Proof of Woodward's Formal Synthesis: Angew. Chem. Int. Ed., 2008, 47, 1736-1740.

Longifolene

Corey: J. Am. Chem. Soc., 1961, 83, 1251-1253.
McMurry: J. Am. Chem. Soc., 1972, 94, 7132-7137.

Atom Economy

Science, 1991, 254, 1471-1477.
Angew. Chem. Int. Ed., 1995, 34, 259-281.

Week 2

A(1,3)-Strain Review: Chem. Rev., 1989, 89, 1841-1860.
Substrate Directed Reactions Review: Chem. Rev., 1993, 93, 1307-1370.
Fürst-Plattner Example 1: Tetrahedron Lett., 1998, 39, 6811-6814.
Fürst-Plattner Example 2: J. Chem. Soc., Perkin Trans. 2, 1978, 627-632.
Fürst-Plattner Example 3: J. Am. Chem. Soc., 1983, 105, 2354–2358.
Fürst-Plattner Electronic Exceptions: J. Am. Chem. Soc., 2000, 122, 168–169.
Dermostatin A: Angew. Chem. Int. Ed., 2001, 40, 3224-3227.

Week 3

Protecting Groups Review: Angew. Chem. Int. Ed. Engl., 1996, 35, 2056-2083.

Week 4

Week 5

Chelate Review: Acc. Chem. Res., 1993, 26, 462-468.
Cram's Rule: J. Am. Chem. Soc., 1952, 74, 5828-5835.
Cram Chelate: J. Am. Chem. Soc., 1959, 81, 2748-2755.
Keck's Lewis Acid study: Tetrahedron Lett., 1984, 25, 265-268.

Week 6

Redox Economy: Angew. Chem. Int. Ed., 2009, 48, 2854-2867.
Asymmetric Borane Reductions: Acc. Chem. Res., 1992, 25, 16-24.
Modified Wolff-Kishner: J. Am. Chem. Soc., 2004, 126, 5436-5445.
Luche Reduction: J. Am. Chem. Soc., 1981, 103, 5454-5459.
Stryker Reduction: J. Am. Chem. Soc., 1988, 110, 291-293.
Directed Borohydride: J. Am. Chem. Soc., 1988, 110, 3560-3578.
Stereochemical Models of Reduction: J. Org. Chem., 1984, 49, 778-788.
Organoborane Reductions: J. Org. Chem., 1988, 53, 2916-2920.
CBS reagent prep: J. Org. Chem., 1993, 58, 2880-2888.
CBS Transition State: Tetrahedron Lett., 2009, 50, 1324-1327.
Chemoselective Aldehyde Reduction: Tetrahedron Lett., 1983, 24, 4287-4290.
Alkoxydialkylborane reductions: Tetrahedron Lett., 1987, 28, 155-158.
Chelate Control: Tetrahedron Lett., 1985, 26, 5139-5142.

Tar-BH

Enantioselective Reductions with Boronic Esters: Tetrahedron Lett., 2007, 48, 9025-9029.
Boronic Ester 2: Synthesis, 2008, 23, 3874-3876.
Boronic Ester 3: Org. Lett., 2009, 11, 4358-4361.

Week 7

IBX Prep: J. Org. Chem., 1999, 64, 4537-4538.
IBX oxidation procedure: Org. Lett., 2002, 4, 3001-3003.
NHC catalyzed oxidation of allylic or benzylic alcohols to esters: Org. Lett., 2007, 9, 371-374.
NHC catalyzed oxidation of aldehydes to esters: Org. Lett., 2008, 10, 4331-4334.
Fetizon's reagent: J. Chem. Soc. D, 1969, 1102-1102.

Tempo

With Cupric Ions and Oxygen: J. Am. Chem. Soc., 1984, 106, 3374-3376.
Primary Selective: Org. Lett., 2001, 3, 3041-3043.
Use in Total Synthesis: Org. Lett., 2004, 6, 3985-3988.
Review: Synthesis, 1996, 10, 1153-1176.
Synthesis of alpha-hetereoatom substituted aldehydes: Tetrahedron Lett. ,1992, 33, 5029-5032.

Week 8

Cyclohexanone alkylation example: Org. Lett., 2007, 9, 2839-2842.
Elemanolides: Tetrahedron, 1988, 44, 1369-1392.
beta-vetivone synthesis: J. Am. Chem. Soc., 1973, 95, 3414-3415.
Evans Auxiliary: J. Am. Chem. Soc., 1982, 104, 1737-1739.

Myers Auxiliary

Week 9

Review: Chem. Soc. Rev., 2004, 33, 65-75.
Boron Enolates: Chem . Letters, 1976, 5, 559-562.
Boron Enolates 2: J. Am. Chem. Soc., 1979, 101, 6120-6123.
Controlling Enolate Geometry: J. Am. Chem. Soc., 1989, 111, 3441-3442.
E-selective enolate formation: J. Am. Chem. Soc., 1991, 113, 9571-9574.
Evans Asymmetric Alkylation: J. Am. Chem. Soc., 1982, 104, 1737-1739.
Evans Asymmetric Aldol Reaction: J. Am. Chem. Soc., 1981, 103, 2127-2129.
Crimmins Auxilliary "Anti-Evans" product: J. Org. Chem., 2001, 66, 894-902.
Magnesium catalyzed anti-Aldol: J. Am. Chem. Soc., 2002, 124, 392-393.
Anti-selective Boron Aldol: J. Am. Chem. Soc., 1997, 119, 2586-2587.
Ghosh anti-Aldol: J. Am. Chem. Soc., 1996, 118, 2527-2528.
Prelog-Djerassi Lactone Synthesis: Tetrahedron Lett., 1982, 23, 807-810.

Acetate Aldol

Sammakia Auxiliary: Org. Lett., 2004, 6, 23-25.
Sammakia Auxiliary 2: J. Org. Chem., 2006, 71, 6262-6265.
Sammakia Auxiliary 3: Org. Lett., 2004, 6, 3139-3141.
Crimmins Auxiliary: Org. Lett., 2007, 9, 149-152.
Olivio Auxiliary: Tetrahedron, 2004, 60, 9397-9403.

Mukaiyama Aldol

Yamamoto Lewis-acid catalyst: J. Am. Chem. Soc., 1991, 113, 1041-1042.
Carreira Lews-acid catalyst: J. Am. Chem. Soc., 1994, 116, 8837-8838.

Week 10

Diels-Alder

Diels-Alder in Total Synthesis: Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
Intramolecular DA: Angew. Chem., Int. Ed. 2001, 40, 820-849.
Intramolecular DA: Synthesis 2002, 2457-2463.
Catalytic Enantioselective DA: Angew. Chem., Int. Ed. 2002, 41, 1650-1667.
Asymmetric DA: J. Am. Chem. Soc. 1988, 110, 1238-1256.
Asymmetric DA: J. Am. Chem. Soc. 1984, 106, 4261-4263.
Diastereoselectivity of DA: Angew. Chem., Int. Ed. 1987, 26, 1184-1186.
Chiral Catalyst DA: J. Am. Chem. Soc. 1993, 115, 6460-6461.
Chiral Organocatalyst DA: J. Am. Chem. Soc. 2000, 122, 4243-4244.
Pumiliotoxin C: Tetrahedron Lett. 1977, 18, 1253-1256.
Pumiliotoxin C: J. Am. Chem. Soc. 1978, 100, 5179-5185.
Estrone: J. Am. Chem. Soc. 1980, 102, 5253-5261.