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N um ber 24 | 2009 C hem C om m Pages 3477–3640 ISSN 1359-7345 1359-7345(2009)24;1-# www.rsc.org/chemcomm Number 24 | 28 June 2009 | Pages 3477–3640 Chemical Communications As featured in: See Takahiro Kawamoto, Sho Hirabayashi, Xun-Xiang Guo, Takahiro Nishimura and Tamio Hayashi, Chem. Commun., 2009, 3528. www.rsc.org/chemcomm Registered Charity Number 207890 Rhodium-catalyzed intermolecular asymmetric hydroalkoxylation and hydrosulfenylation of

Epoxidation, Dihydroxylation, and the Utility of Epoxides and Diols Ready Outline: Epoxidation Condensation approaches Darzens condensation Sulfur ylides With organic peroxides Peroxy acids Peroxy iminic acids Dioxiranes DMDO Enantioselective versions Metal-catalyzed Approaches V(O)(acac)2 Sharpless AE Metal Oxo’s MTO Fe, Pt and Mn-based (Salen)Mn Jacobsen AE Epoxide Ring Opening Opening under acid or basic conditions Organocopper additions Reactions of epoxy alcohols Dihydroxylation

3896 Published OnlineFirst on May 11, 2010 as 10.1158/0008-5472.CAN-09-3995 Integrated Systems and Technologies Cancer Research β-Lapachone Micellar Nanotherapeutics for Non–Small Cell Lung Cancer Therapy Elvin Blanco1, Erik A. Bey1,2, Chalermchai Khemtong1, Su-Geun Yang1, Jagadeesh Setti-Guthi1, Huabing Chen1, Chase W. Kessinger1, Kevin A. Carnevale3, William G. Bornmann4, David A. Boothman1,2, and Jinming Gao1 Abstract Authors' A Oncology, Texas So 3Departme of South C Experiment Center, Ho

Reactivity Umpolung-1 Ready Reactivity Umpolung: reversal of normal polarity electrophiles become nucleophiles nucleophiles become electrophiles Outline: 1. electrophilic heteroatoms 2. acyl anions 3. homoenolates 4. the cyclopropane trick 5. sulfone chemistry Normal reactivity: X x = heteroatom d = donor (Nu-) a = acceptor (E+) d a d a d X X X X or 1 3 1 5 How to make: X X or X X 1 2 1 4 complimentary

MRI-Visible Micellar Nanomedicine for Targeted Drug Delivery to Lung Cancer Cells Jagadeesh Setti Guthi,†,‡ Su-Geun Yang,†,‡ Gang Huang,† Shunzi Li,†,§ Chalermchai Khemtong,† Chase W. Kessinger,† Michael Peyton,†,| John D. Minna,†,§,| Kathlynn C. Brown†,§, and Jinming Gao*,† Department of Pharmacology, Simmons ComprehensiVe Cancer Center, Department of Internal Medicine, DiVision of Translational Research, and Hamon Center for Therapeutic Oncology Research, UniVersity of Texas Southwestern

Oxidations at Carbon General references March, Advanced Org Chem, 1992, 1158-1238 Trost, Comp. Org. Syn. 1991, vol 7 Carey and Sundberg, Advanced Org Chem, part B, 615-664 Smith, Org Syn, Chap 3 H CH3 C(-IV) R CH3 C(-III) R CH2 OH C(-1) R CH OH RR H2 C R C(-II) R C O R C(0) R CH O C(+I) H CH2 OH C(-II) H CH O C(0) C(II) R COR O C(+III) H COH O C(+II) O C O C(+IV) RO COR O C(+IV) alkane RCH2M RCH2SiR3 RCH2X X=halide RCH2NR2 RCH2SR RCH2PR2 Acetal: RCH(OR)2

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Reagent/Reaction Use Ref Note DMSO/DCC (Pfitzner- Moffatt or Moffatt) Alcohol ketone/aldehyde Jacs 1963, 3027; Mech: JACS, 1965, 5561, JOC, 1967, 1926 First DMSO-based; DCC pain to remove; EDCI better DMSO/Ac2O “ Jacs 1967, 2416 DMSO/TFAA “ Jacs, 1975, 2758 DMSO/SO3-Pyridine (Parikh- Doering) “ JACS, 1967, 5505 Often under ambient conditions; best for α-chiral aldehydes/ketones (COCl)2/DMSO (swern) “ JOC, 1978, 2480; mech: Tet. 1978, 1651 Most commonly used; DMSO/Ac2O