James D. White. A very productive professor 64 students graduated from his lab 94 postdocs have worked in his lab. Education Experience
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1 A very productive professor 64 students graduated from his lab 94 postdocs have worked in his lab Education Experience Fraser Fleming University of Drexel Pavel agory University of Michigan Cambridge University, B.A University of itish Columbia, M.c Massachusetts nstitute of Technology, Ph.D (with G. Büchi). Professional Experience nstructor, arvard University, Assistant Professor, arvard University, Rich Carter Mitchell Avery Associate Professor, arvard University, University of Mississippi regon tate University Associate Professor, regon tate University, Professor, regon tate University, Distinguished Professor, regon tate University, Distinguished Professor Emeritus, regon tate University, 2003-present. A very stubborn total synthesis professor More than 60 natural products (including analogues) have been synthesized in 43 years, no more than 36 methodology papers have Alexandre Yokochi Xuegong he been published (just for fun?) regon tate University Lanzhou University
2 A novel chiral ligand R 3 R 3 M Å 4.00 Å 4.27 Å Acc. Chem. Res. 2016, 49, 1825 ynthesis. 2016, 48, 2768 M=Co, =t-bu =, R 3 = 2 CC 2 cat. 5 mol% KAc 5 mol% DCM, r.t. [C/] M=Cr, =t-bu =t-bu, R 3 = TM 87-97% yield 83-98% ee [C/] cat. 5 mol% 3 Å M t-bu/ph 2-30~-20 o C >91% yield >92% ee cat. 10 mol% TM, Mn, 3 Å M TF, then aq. >92% yield 69-97% ee C 2 rg. Lett. 2014, 16, 3880 M=Fe, =t-bu =t-bu, R 3 = M=Fe, =t-bu =t-bu, R 3 =n-bu M=Cu, =t-bu =t-bu, R 3 = R alkyl\aryl rg. Lett. 2011, 13, 2488 C 3 2 R 3 R 4 R 4 cat. 10 mol% AgBF 4 10 mol% DCE, r.t % yield 82-98% ee cat. 20 mol% DCE, -5 o C 89-98% yield >93% ee cat. 7.5 mol% C 3, 50 o C >80% yield >90% ee cat. 10 mol% 4 Å M,, 40 o C 81-99% yield >91% ee R 4 R 3 R 4 rg. Lett. 2015, 17, 4564 R J. Am. Chem. oc. 2014, 136, C() 2 R 4 a R o C >90% yield 120 o C DM Chem. ci. 2014, 5, rg. Lett. 2012, 14, Pb(Ac) 4 2 R 4 R 3 ~80% yield Tetrahedron. Lett. 1974, 38, 3361 J. Am. Chem. oc. 1975, 97, 451 J. Am. Chem. oc. 1977, 99, 1172 (C) 2 DMAP then C 2 C 2 C hv R 3 C 2 C 2 R 3 [22] esterification Tetrahedron. Lett. 1980, 21, 3174
3 hv is critical to good yield 1. o- 2 C 6 4 C 2 2. hv 1. deprotect ~70% yield 2. Ph 2 R benzene, heat 1 J. rg. Chem. 1975,40, 909. J. rg. Chem. 1975,40, LDA, 2. LMD, Phe % 2 2 Tetrahedron. Lett. 1993, 34, one diastereomer 1. o- 2 C 6 4 C 2 2. TB 3. 3 C 2 (C 2 ) 2 TM 4. hv 2 TB TM J. rg. Chem. 1990,55, C 2 Carbapenem P-5 olandelactone E and F J. rg. Chem. 2008,73, rg. Lett. 2007, 9, Chem. Commun., 2000, 1263 J. Chem. oc., Perkin Trans. 1, 2001, Constanolactone A and B J. Am. Chem. oc. 1995, 117, Loline phorboxazole A rg. Biomol. Chem. 2012, 10, rg. Lett. 2001, 3, rg. Lett. 2006, 8, rg. Lett. 2006, 8, Rapamycin J. rg. Chem. 1996, 61, Tetrahedron. 2009, 65, Botryococcene J. Am. Chem. oc. 1988, 110, J. Chem. oc. Perkin. Trans , Epicylindrospermopsin J. Am. Chem. oc. 2002, 124, J. rg. Chem. 2005, 70, Latrunculin A J. Am. Chem. oc. 1990, 112, J. rg. Chem. 1992, 57, uperzine A J. rg. Chem. 2015, 80, rg. Lett. 2013, 15, 882.
4 B Boromycin 3 J. Am. Chem. oc. 1989, 111, 790. J. Am. Chem. oc. 1983, 105, Verrucarol J. rg. Chem. 1981, 46, ynthesis. 1998, 619. ntegerrimine J. rg. Chem. 1986, 51, J. rg. Chem. 1992, 57, Avermectin B 1a J. Am. Chem. oc. 1990, 112, J. Am. Chem. oc. 1995,117, C 2 Ac Providencin J. rg. Chem. 2014, 79, 700. rg. Lett. 2009, 11, C 2 Prelog-Djerassi Lactone J. Am. Chem. oc. 1979, 101, 226. Euonyminol J. Am. Chem. oc. 1995,117, J. Am. Chem. oc. 1997,119, Monic Acid J. rg. Chem. 1988, 53, Byssochlamic Acid J. Am. Chem. oc. 1992, 114, J. Am. Chem. oc. 2000, 122, Kendomycin rg. Lett. 2005, 7, 235. olandelactone E and F n 2 C Constanolactone A and B n 2 C 1. Li TF/ 2 2. n 4 n n C 2 n-bu 3 n AB C 2 C 2 Bu 3 n 1.5:1 desired ynlett. 1996, Pd 2 (C) 2 C 2 2. t-bu ()-diethyltartrate Ti(i-Pr) 4 n % yield 2 C not obtained 2 C E:Z=4:1 C 2
5 RCM Ph 3 C, 3 2. CCC 2 TB BF TB, imidazole 4. TBAF/TF Tr TB 1. aal 2 (C 2 C 2 C 3 ) 2 2. Ms, Li Tr 3. Bu 3 nli 4. TBAF/TF nbu 3 Tf 2 /DCM Tr 2 C TBDP Tr 7.6:1 C 2 1. B Ph 3 C, 3 3. TB, imidazole TE 4. DBAL 5. TPAP, M Byssochlamic Acid 1. C 2 CMg 2. Ac TF/ 2 1. hv, Ph 2 C 2. aq. a 2 C 3 then aq. 3. C 2 2 Tf Tr Tf Tr Tf To increase Tr stereoselectivity, > cis-olefin may be >> a better substrate nbu Bu 3 n 3 Bu 3 n disfavored nbu 1. (CF3 C 3 2 ) 2 P()C 2 C 2 2. DBAL Tf 2 /DCM Tr 3. Ms, Li Tr TB Tr 4. Bu 3 nli 5. TBAF/TF exclusively TBDP 1. a, () 2 C isomers C 2 C 2 C 2 1. hv, DCM 2. Δ, toluene 1. a/ 2. LA 1. DBU 2. aq. Li 3. aq. ( 3 C) 2 C 3, Py 2 C C 2 Pr C 2 no isolation TBDP C 2 3 DCC, Δ, DMAP Pr Epicylindrospermopsin Cp 2 Ti 2 toluene, Δ Tf Tr nbu 3 strongly disfavored Tr PG Pr 2 2
6 Bn 2 n-buli, Ce 3 Botryococcene ntegerrimine =p-c 6 4 C 2 Bn 2 1. cis-2-butene n-buli, ()B(pc) 2 2. Ms 2, Py 2 TB 1. MM 2. LA 1. TBTf, TB 3 1. Ph 3 C, 3 Tr 2. C , Pd() 2 /C 2. L-electride Bn 2 4. Boc 2, 3 Boc 5. TPAP, M Ms 1. Zn, 4 2. / MM 1. EM EM 2. LA C 2 3. wern [] 4. Mg 5. wern [] 1. / 2. LA 3. PCC [] 4. Eschenmoser s salt 5. ab 4 1. p-ts 2. KC 3. DBAL 1. a 3, Δ 2. C MM MM Boc TB 1. p-c 6 4 C 2. m-cpba Tetrahedron. 1985, 41, toluene M, Δ 1. C(C 3 )C 2 MM MM 2. K 3. MM 2 C 1. C 2 CMg 2. TBAF 3. Ts C 2 4. a, Δ 5. Ac 2 1. Ti(iPr) 4 (-)-DPT, t-bu 2. 3,5-DB chloride 3. LA 4. 3,5-DB chloride Ac MM /M Δ Boc TB exo addition J. rg. Chem. 1976, 41, LDA 2. aq. 4 BD 3. a 4 4. C 2 2 DB LDA MAP C 2 MM C 2C C 3 Both methods require 14 steps in total C 2 1. a 4 2. K 2 C a 4 5. C 2 2 Maybe a better starting material?
7 5. ab 4 TBDM TBDM B Boromycin TM TM TM TM 3 TBDM TBDM TBDM TBDM TBDM TBAF/TF TBDM TBDM TBDM TM 1. TBAF/TF 2. DMAP C 3 TBDM TBDM 1. TM 2. m-cpba J. rg. Chem. 1996, 61, Base R1 Base TBDM TBDM TBDM 2 LiMD TMTf Chan rearrangement serves as a useful tool to synthesize moiety Tetrahedron. Lett. 1984, 25, uperzine A aza-prins eph 1. a 4 2. Ag 2 C 3 1. Ag 2 2. hv 1. Zn, a 2. DMP 3. Mg 4. DMP 1. TP KMD 2. Ph TM 3 1. TP 3 2. eph C 2 3, 5-DB chloride ( 2 CF 3 ) 2 2. () 4 Pd (n 3 ) 2 1. LA KMD TP eph 1. Al 3, Δ 2. F
8 2 C 2 p-ts, Δ C 2 Providencin Ac C 2 Cargill rearrangement Acc. Chem. Research. 1974, 7, 106. p-ts 1. Mg 2. P 3 /Py 22 cycloaddition? electivity issue atural occurring chiral center? J. Am. Chem. oc. 1993, 115, rg. Lett. 2002, 4, rg. Lett. 2005, 7, TP 2. DDQ 3. Ts 4. s 4, M a 4 5. Piv/Py Piv 6. Ac 2 /Py PMB TB TP 1. n 2 /a Ac 2. DMP Cp 2 Zr TB C Piv 2 C TB () 4 Pd 1. PMB/a 2. Ac/ 2 3., 2 imidazole PMB TM C 2 toluene, Δ L Pd L PMB Zr Cp Cp TB F 3 B disfavored TP Ag 3 silica Ac Piv TB TP Ac Cp 2 Zr 2 n-buli PMB TB 2 2 C 1. / 2. TBTf PMB TB PMB Cp Zr Verrucarol Aldol disconnection? 1. (C 2 ) 2 CA C C 2. hv TB favored Zr Cp Cp PMB PMB TB TB 2 C C C Macrolide Core of Latrunculin A Many natural macrolide contains repeating alkenes with E, E, Z or E, Z geometry equential wittig olefination? u
9 , r.t. Tetrahedron. 1995, 51, Tetrahedron. Lett. 1992, 33, 557. Ph 2 C 2 R R C applicable substrate but selectivity is low LDA, -78 o C LDA, -78 o C Li Li For both aryl and alkyl aldehyde, the yields are above 47% (67% as the highest) When is alkyl group, geometry selectivity is very good (E:Z > 8:1) owever if is aryl group, geometry selectivity is much lower (E:Z~2:1) Li C workup Euonyminol C 2 TB LDA 15-crown-5 Mg C C 2 Mg C 2 TB TBTf 3 Ag 2 C 2 Mg TB C 6 6, Δ ne diastereomer C 2 TB C 2 TB B (PhC 2 ) 2 C 2 TB C 2 TB t-bu V(acac) 2 V 3 C 2 TB C 2 TB ab 4 Ce 3 3:1 C 2 TB C 2 TB TFA C 2 TB CF 3 C 2 CCF 3 1. Py/ 2 TB 2. imidazole PhC() 2 PPT, Δ TB Ph TB TBAF Ph TB Ph TB KMD Davis s oxaziridine Ph TB 3 Al quantitative Ph 4:1 1. LA TB aq. 2. TBTf 3 R R R Ph R. s 4 2. Ac Ac 2 Ac Ac Ac Ac Ac Ac Ac Ac
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